1,2-Dichloroethane → 3-[(2-Methylprop-2-en-1-yl)oxy]azetidine hydrochloride

HRID 82950Notes

Reaction equation

C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([O:12][CH2:13][C:14]([CH3:16])=[CH2:15])[CH2:9]2)C=CC=CC=1.[Cl:23]CCCl.ClC(OC(Cl)C)=O>CO>[ClH:23].[CH3:16][C:14](=[CH2:15])[CH2:13][O:12][CH:10]1[CH2:11][NH:8][CH2:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

A 16 mL flask was charged with 1-(diphenylmethyl)-3-[(2-methylprop-2-en-1-yl)oxy]azetidine (276 mg, 0.94 mmol; which may be prepared as described in Step 1) and 1,2-dichloroethane (4.1 mL). 1-Chloroethyl chloroformate (135 μL, 1.24 mmol) was added and the reaction mixture was stirred at 70° C. for 1.5 h. After cooling to room temperature, methanol (4.1 mL) was added and the reaction mixture was stirred at 70° C. for 1.5 h. The reaction mixture was concentrated to dryness and the residue was triturated in pentane to give the final product (192 mg, quantitative) as a brown oil.

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 residue was triturated in pentane

Sources & evidence

ORD record: ord-ac5eee5b523445c7b5b2ca05a5dd90c7
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846711B2

Reaction notes

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