1,2-Dichloroethane → 3-(2-Thienylmethoxy)azetidine hydrochloride

HRID 2171986

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A 50 mL flask was charged with 1-(diphenylmethyl)-3-(2-thienylmethoxy)azetidine (204 mg, 0.61 mmol; which may be prepared as described in Step 2) and 1,2-dichloroethane (2.7 mL). 1-Chloroethyl chloroformate (86 μL, 0.79 mmol) was added and the reaction mixture was stirred at 70° C. for 1.5 h. After cooling to room temperature, methanol (2.7 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 mixture was triturated in pentane to give a dark wax (140 mg, quantitative) which was used without further purification.

Workup

temperatureAfter cooling to room temperature
stirringthe reaction mixture was stirred at 70° C. for 1.5 h
concentrationThe reaction mixture was concentrated to dryness
customThe crude mixture was triturated in pentane
customto give a dark wax (140 mg, quantitative) which
customwas used without further purification

Sources & evidence

ORD record: ord-1b19963750ac4979891e4080cf839359
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051321B2

Linked notes

Loading…