1,2-Dichloroethane → 3-Phenoxyazetidine hydrochloride

HRID 633872Notes

Reaction equation

HRID 633872 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)C=CC=CC=1.[Cl:25]CCCl.ClC(OC(Cl)C)=O>CO>[ClH:25].[O:12]([CH:10]1[CH2:11][NH:8][CH2:9]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5213051-Chloroethyl chloroformateHCID 28175781-Benzhydryl-3-phenoxyazetidine

Product 1

HCID 185264463-Phenoxyazetidine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A 50 mL flask was charged with 1-(diphenylmethyl)-3-phenoxyazetidine (328 mg, 1.04 mmol; which may be prepared as described in Step 2) and 1,2-dichloroethane (4.6 mL). 1-Chloroethyl chloroformate (164 μL, 1.35 mmol) was added and the reaction mixture was stirred at 70° C. for 1.5 h. After cooling to room temperature, MeOH (4.6 mL) was added and the reaction mixture was stirred at 70° C. for 1.5 h. The reaction mixture was concentrated to dryness. The crude product was triturated in pentane to give the title compound (204 mg, quantitative) as pale yellow crystals. This product was used in the next step without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe reaction mixture was stirred at 70° C. for 1.5 h
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customThe crude product was triturated in pentane

Sources & evidence

ORD record
ord-1d493b49cd1d483da3b72ecda0293c06
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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