Cyclopentylamine → cyclopentyl-carbamic acid ethyl ester

HRID 2361875Notes

Reaction equation

HRID 2361875 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10](Cl)=[O:11])[CH3:8].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:7]([O:9][C:10](=[O:11])[NH:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:8]

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 10928Ethyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 4193626cyclopentyl-carbamic acid ethyl esterYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cyclopentylamine (5.8 mL, 59 mmol, 1.0 eq.) in CH2Cl2 (250 mL) at room temperature was added ethylchloroformate (7.3 mL, 1.3 eq.) followed by an aqueous solution of K2CO3 (37 g in 500 mL of H2O). The mixture was stirred vigorously for 1 h. The separated aqueous layer was extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and concentrated to give cyclopentyl-carbamic acid ethyl ester (9.6 g, 88%).

Workup

  1. extractionThe separated aqueous layer was extracted twice with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ca6aed742fe14b7dac439effce0674d1
Source dataset
uspto-grants-2014_04
Patent number
US08691814B2

Reaction notes

Loading…