1-N-Boc-cis-1,4-cyclohexyldiamine Chemical Properties

Boiling point:

322.1±31.0 °C(Predicted)

Density 

1.02±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

powder

pka

12.44±0.40(Predicted)

color 

Off-white

Water Solubility 

Soluble in methanol, ethyl acetate and Slightly soluble in water.

InChI

InChI=1S/C11H22N2O2/c1-11(2,3)15-10(14)13-9-6-4-8(12)5-7-9/h8-9H,4-7,12H2,1-3H3,(H,13,14)/t8-,9+

InChIKey

FEYLUKDSKVSMSZ-DTORHVGOSA-N

SMILES

C(OC(C)(C)C)(=O)N[C@@H]1CC[C@H](N)CC1

CAS DataBase Reference

247570-24-7

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2921309990

1-N-Boc-cis-1,4-cyclohexyldiamine Usage And Synthesis

Uses

cis-4-(Boc-amino)cyclohexylamine can be used in agrochemical, pharmaceutical and dyestuff field.

Synthesis

Step 4: To a solution of tert-butyl (cis-4-azido-cyclohexyl)-carbamate (6.3 g, 26 mmol) in methanol (100 mL) was added 5% Pd/C (Degussa type, 0.63 g) under argon protection. The reaction flask was sealed, evacuated and backfilled with hydrogen, and the process was repeated three times. The reaction mixture was stirred for 2 h at room temperature under an atmosphere of hydrogen at 1 atm. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure. The residue was partitioned between ether (Et2O) and 1N hydrochloric acid (HCl) solution. The aqueous phase was separated and alkalized with sodium hydroxide solution to pH > 10, followed by extraction with ethyl acetate (EtOAc, 2 × 100 mL). The organic phases were combined, washed with saturated sodium chloride solution (brine), dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to afford the white solid product (tert-butyl cis-4-amino-cyclohexyl)-carbamate (3.6 g, 64% yield). Mass spectrometry (MS) analysis showed (M+H)+ = 215.6.

References

[1] Patent: US2005/54626, 2005, A1. Location in patent: Page/Page column 48
[2] Patent: EP1683795, 2006, A1. Location in patent: Page/Page column 14; 15
[3] Patent: US2005/20639, 2005, A1. Location in patent: Page 14 - 15

1-N-Boc-cis-1,4-cyclohexyldiamine(247570-24-7)Related Product Information

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