Phenyl chloroformate → Phenyl carbamate

HRID 1182119Notes

Reaction equation

HRID 1182119 reaction equation
FC1C=CC(OC2C[N:9](CCCN)C2)=CC=1.[C:17]1([O:23][C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C1C=CC=CN=1)C>ClCCl>[C:17]1([O:23][C:24](=[O:25])[NH2:9])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 218852-DimethylaminopyridineHCID 69410452HCID 69410452, compound

Product 1

HCID 69322Phenyl carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propylamine (0.05 g, 0.223 mmol), phenylchloroformate (0.056 ml, 0.446 mmol) and dimethylaminopyridine (0.027 g, 0.223 mmol) in dichloromethane (4 ml) is stirred at ambient temperature for 24 hours. The reaction mixture is evaporated and the crude product purified by flash silica chromatography (elution 5:95 methanol/dichloromethane) to afford 3-[3-(4-Fluoro-phenoxy)-azetidin-1-yl]-propyl)-carbamic acid phenyl ester. [MH]+ 344.9.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe crude product purified by flash silica chromatography (elution 5:95 methanol/dichloromethane)

Sources & evidence

ORD record
ord-9c1023b8e6fb41e28162afe5787062e2
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

Loading…