Ethanol → 3-(Benzo[b]thiophen-3-yloxy)azetidine hydrochloride
Reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][C:26]2[C:27]3[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=3[S:29][CH:30]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[S:29]1[CH:30]=[C:26]([O:25][CH:23]2[CH2:24][NH:21][CH2:22]2)[C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]1=2Participants
5
Conditions
- Temperature
- 0 °C
Procedure
1-Chloroethyl chloroformate (67.3 μL, 0.621 mmol) was added to a solution of 1-benzhydryl-3-(benzo[b]thiophen-3-yloxy)azetidine (220 mg, 0.592 mmol) in dichloromethane (5 mL) at 0° C. The reaction mixture was stirred for 2 hours at 0° C. and for 5 hours at room temperature. Ethanol (5 mL) was added and the reaction mixture was stirred for 1 hour at 40° C. After concentration to dryness, the crude mixture was precipitated from a mixture dichloromethane/pentane to afford a pale orange solid (140 mg, quantitative) which was used without further purification.
Workup
- stirringthe reaction mixture was stirred for 1 hour at 40° C
- concentrationAfter concentration to dryness
- customthe crude mixture was precipitated from a mixture dichloromethane/pentane
- customto afford a pale orange solid (140 mg, quantitative) which
- customwas used without further purification
Sources & evidence
- ORD record
- ord-a1d2f4ada6f64e6d9cdfe4e5131cd6d8
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846711B2
Reaction notes
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