1,2-Dichloroethane → 3-Phenoxyazetidine hydrochloride

HRID 82916Notes

Reaction equation

HRID 82916 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-74720985648f4e0e9f665b61b036babf
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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