4-AMINO-1-BOC-PIPERIDINE-4-CARBOXAMIDE
- Product Name
- 4-AMINO-1-BOC-PIPERIDINE-4-CARBOXAMIDE
- CAS No.
- 288154-18-7
- Chemical Name
- 4-AMINO-1-BOC-PIPERIDINE-4-CARBOXAMIDE
- Synonyms
- 1-Boc-4-aMinopiperidine-4-carboxaMide;4-AMINO-1-BOC-PIPERIDINE-4-CARBOXAMIDE;1-Boc-4-amino-4-(aminocarbonyl)piperidine;4-chloro-2,3-dihydro-1H-indene-5-carboxylicacid;tert-Butyl 4-amino-4-carbamoylpiperidine-1-carboxylate;4-amino-4-carbamoyl-1-piperidinecarboxylic acid tert-butyl ester;tert-butyl 4-amino-4-carbamoylpiperidine-1-carboxylate - [B86394];1-Piperidinecarboxylic acid, 4-amino-4-(aminocarbonyl)-, 1,1-dimethylethyl ester
- CBNumber
- CB7487316
- Molecular Formula
- C11H21N3O3
- Formula Weight
- 243.3
- MOL File
- 288154-18-7.mol
4-AMINO-1-BOC-PIPERIDINE-4-CARBOXAMIDE Property
- Boiling point:
- 410.8±45.0 °C(Predicted)
- Density
- 1.163±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2–8 °C
- pka
- 15.80±0.20(Predicted)
Safety
- HazardClass
- IRRITANT
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H315Causes skin irritation
H318Causes serious eye damage
H335May cause respiratory irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P310Immediately call a POISON CENTER or doctor/physician.
P321Specific treatment (see … on this label).
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P362Take off contaminated clothing and wash before reuse.
N-Bromosuccinimide Price
- Product number
- B415478
- Product name
- tert-Butyl4-Amino-4-carbamoylpiperidine-1-carboxylate
- Packaging
- 50mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- FA52016
- Product name
- 4-Amino-1-Boc-piperidine-4-carboxamide
- Packaging
- 500mg
- Price
- $80
- Updated
- 2021/12/16
- Product number
- FA52016
- Product name
- 4-Amino-1-Boc-piperidine-4-carboxamide
- Packaging
- 1g
- Price
- $120
- Updated
- 2021/12/16
- Product number
- W5146
- Product name
- tert-Butyl4-amino-4-carbamoylpiperidine-1-carboxylate
- Packaging
- 5g
- Price
- $227
- Updated
- 2021/12/16
- Product number
- 058262
- Product name
- tert-Butyl 4-amino-4-carbamoylpiperidine-1-carboxylate
- Purity
- >95%
- Packaging
- 500mg
- Price
- $843
- Updated
- 2021/12/16
4-AMINO-1-BOC-PIPERIDINE-4-CARBOXAMIDE Chemical Properties,Usage,Production
Synthesis
288154-17-6
288154-18-7
The general procedure for the synthesis of 1-Boc-4-amino piperidine-4-carboxamide from tert-butyl 4-benzyloxycarbonylamino-4-carboxamide piperidine-1-carboxylate was as follows: firstly, 4-(benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1A, 2.0 g, 1.0 eq.) was solubilized in DME (0.5 M), NMM (1.0 eq.) and IBCF (1.0 eq.) and reacted at -15 °C for 10 min. Subsequently, ammonia (1.5 eq.) was added and the reaction mixture was stirred at room temperature for 1.5 hours. After the completion of the reaction was confirmed by LCMS analysis, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The residue was purified by crystallization from ether to afford tert-butyl 4-(benzyloxycarbonylamino)-4-carbamoylpiperidine-1-carboxylate (1B, 70% yield). Next, 1B (1.0 equiv.) and a catalytic amount of acetic acid were dissolved in MeOH (0.05 M) and hydrogenated at 50 °C through an H-cube hydrogenator equipped with a Pd/C column. After completion of the reaction, methanol was removed under reduced pressure and the product was washed twice with cold ether to afford tert-butyl 4-amino-4-carbamoyl piperidine-1-carboxylate (1C, 90% yield). Then, 1C (0.3 M) was mixed with 2-chloro-1,1,1-trimethoxyethane (4.0 eq.) and acetic acid (2.0 eq.) and stirred at 118 °C for 12 hours. After removal of the solvent under reduced pressure, the residue was purified by crystallization from cold ether to afford tert-butyl 2-(chloromethyl)-4-oxo-1,3,8-triazaspiro[4.5]dec-1-ene-8-carboxylate (1D, 67% yield). 1D was dissolved in a 2.0 M solution of ammonia in 2-propanol (0.04 M), an excess of ammonia was drummed in and heated at 60 °C for 12 hours. After confirming the completion of the reaction by LCMS analysis, the solvent was removed to afford tert-butyl 2-(aminomethyl)-4-oxo-1,3,8-triazaspiro[4.5]dec-1-ene-8-carboxylate (1E), which could be used without further purification (ESI-MS: m/z 283.1 [M + H]+). Finally, 1E (1.0 eq.) was dissolved in CH2Cl2, and CH2Cl2/TFA solution (2:1, final concentration 0.15 M) was slowly added at 0 °C. The reaction was confirmed to be complete within 30 min at 0 °C by LCMS analysis. Volatiles were removed under reduced pressure to afford the TFA salt of 2-(aminomethyl)-1,3,8-triazaspiro[4.5]dec-1-en-4-one (1G), which was used without further purification (ESI-MS: m/z 183.1 [M + H]+).
References
[1] Journal of Medicinal Chemistry, 2000, vol. 43, # 12, p. 2387 - 2394
[2] Patent: US2009/253725, 2009, A1. Location in patent: Page/Page column 51
[3] Patent: WO2006/41830, 2006, A2. Location in patent: Page/Page column 61
[4] Patent: WO2006/44504, 2006, A1. Location in patent: Page/Page column 98
4-AMINO-1-BOC-PIPERIDINE-4-CARBOXAMIDE Preparation Products And Raw materials
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