1-Chloroethyl chloroformate → Azetidin-3-yl(4-chlorophenyl)methanone hydrochloride

HRID 1182087Notes

Reaction equation

HRID 1182087 reaction equation
C([N:14]1[CH2:17][CH:16]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[O:19])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClCCl>[ClH:26].[NH:14]1[CH2:17][CH:16]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[O:19])[CH2:15]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 69361102(1-Benzhydryl-azetidin-3-yl)-(4-chloro-phenyl)-methanone

Product 1

HCID 69358091Azetidin-3-yl(4-chlorophenyl)methanone hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1-Benzhydryl-azetidin-3-yl)-(4-chloro-phenyl)-methanone (19.8 g, 54.8 mmol) in dichloromethane (250 ml), cooled to −4° C., is treated with 1-chloroethylchloroformate (8.0 ml, 73.8 mmol) and allowed to warm to ambient temperature. The reaction mixture is stirred for 18 hours and then evaporated. The residue is dissolved in methanol (220 ml) and stirred at ambient temperature for 3.5 hours. The methanol solution is concentrated and the product precipitated by addition of diethylether. The precipitate is collected by filtration and dries under high vacuum to afford Azetidin-3-yl-(4-chloro-phenyl)-methanone hydrochloride. [MH]+ 195.95.

Workup

  1. customevaporated
  2. dissolutionThe residue is dissolved in methanol (220 ml)
  3. stirringstirred at ambient temperature for 3.5 hours
  4. concentrationThe methanol solution is concentrated
  5. customthe product precipitated by addition of diethylether
  6. filtrationThe precipitate is collected by filtration and dries under high vacuum

Sources & evidence

ORD record
ord-650a3f69dbc245e8888a830ff0612043
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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