TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE Chemical Properties

Melting point:

158-160

Boiling point:

384.4±31.0 °C(Predicted)

Density 

1.123±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

16.40±0.20(Predicted)

color 

White to Almost white

InChI

InChI=1S/C11H20N2O3/c1-11(2,3)16-10(15)13-6-4-8(5-7-13)9(12)14/h8H,4-7H2,1-3H3,(H2,12,14)

InChIKey

YHFUWPUJUMZXBD-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(C(N)=O)CC1

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

29333990

TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE Usage And Synthesis

Uses

1-BOC-piperidine-4-carboxamide is a common organic synthon in which the Boc group can be removed under acidic conditions, releasing the cyclohexylamine structure. Furthermore, the formamide structure on the ring can be converted to a cyano group under certain reaction conditions; and the oxygen atom on the formamide can be converted to a sulfur atom by the action of Lawesson reagent.

Chemical Properties

White powder

Synthesis

General procedure for the synthesis of tert-butyl 4-carbamoylpiperidine-1-carboxylate from 1-Boc-4-piperidinecarboxylic acid: a mixture of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (220 mg, 2.88 mmol), ammonium chloride (154 mg, 2.88 mmol), EDCI (367 mg, 1.92 mmol) and HOAT (195 mg. 1.44 mmol) were dissolved in dichloromethane (10 mL) at 0 °C, followed by dropwise addition of DIPEA (1.0 mL, 5.77 mmol). After dropwise addition, the reaction mixture was stirred at room temperature for 10 hours. After completion of the reaction, the reaction mixture was washed with distilled water (10 mL x 3). The organic layer was separated and dried with anhydrous Na2SO4 and subsequently concentrated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as eluent to afford tert-butyl 4-carbamoylpiperidine-1-carboxylate as a white solid (160 mg, 73% yield).1H NMR (400 MHz, CD3OD): δ 4.11 (d, J = 13.4 Hz, 2H), 2.76-2.86 (m, 2H), 2.38-2.45 ( m, 1H), 1.79 (d, J = 11.2 Hz, 2H), 1.52-1.62 (m, 2H), 1.47 (s, 9H).MS-ESI: m/z 173.20 [M-55]+.

References

[1] Patent: WO2016/34134, 2016, A1. Location in patent: Paragraph 00539
[2] Patent: CN105399698, 2016, A. Location in patent: Paragraph 1621-1623
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9196 - 9213
[4] Patent: WO2015/48662, 2015, A2. Location in patent: Page/Page column 114
[5] European Journal of Medicinal Chemistry, 1984, vol. 19, # 2, p. 181 - 186

TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE(91419-48-6)Related Product Information

• 1-N-BOC-PIPERIDINE-3-CARBOXAMIDE
• 1-Boc-4-cyanopiperidine
• (+/-)-1-N-BOC-PIPERIDINE-2-CARBOXAMIDE
• 1-TERT-BUTYL 2-METHYL PIPERIDINE-1,2-DICARBOXYLATE
• N-BOC-3-Aminopiperidine
• 1-BOC-3-PIPERIDINECARBOXALDEHYDE
• N-Boc-4-piperidinemethanol
• 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde
• N-BOC-piperidine-4-carboxylic acid
• N-Boc-2-piperidinecarboxylic acid
• Ethyl N-Boc-piperidine-4-carboxylate
• Ethyl 1-Boc-piperidine-2-carboxylate
• 1-Boc-3-hydroxypiperidine
• N-Boc-Piperidine-4-carboxylic acid methyl ester
• N-Boc-piperidine-3-methanol
• N-Boc-piperidine-2-methanol
• 1-Boc-4-Methylaminopiperidine
• 1-Boc-3-piperidone