Ethanol → 3-(Benzofuran-7-yloxy)-azetidine hydrochloride

HRID 83066Notes

Reaction equation

HRID 83066 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][C:26]2[C:34]3[O:33][CH:32]=[CH:31][C:30]=3[CH:29]=[CH:28][CH:27]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[O:33]1[C:34]2[C:26]([O:25][CH:23]3[CH2:24][NH:21][CH2:22]3)=[CH:27][CH:28]=[CH:29][C:30]=2[CH:31]=[CH:32]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformateHCID 671544751-Benzhydryl-3-(benzofuran-7-yloxy)-azetidine

Product 1

HCID 671547083-(Benzofuran-7-yloxy)-azetidine hydrochlorideYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (107 μL, 0.99 mmol) was added to a solution of 1-benzhydryl-3-(benzofuran-7-yloxy)-azetidine (349 mg, 0.98 mmol) in dichloromethane (10 mL) at 0° C. The reaction mixture was stirred for 4 hours at room temperature. Ethanol (10 mL) was added and the reaction mixture was stirred for an additional 2 hours at room temperature and 3 hours at 40° C. After concentration to dryness, the residue was taken in a mixture dichloromethane/diethyl ether to afford the title compound as a white solid (193 mg, 87%).

Workup

  1. stirringthe reaction mixture was stirred for an additional 2 hours at room temperature and 3 hours at 40° C
  2. concentrationAfter concentration to dryness

Sources & evidence

ORD record
ord-c6991bf548e74d89a02674fb435a9bdc
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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