Bicifadine → 3-Cyclopropanecarbonyl-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane

HRID 66276Notes

Reaction equation

[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]23[CH2:12][CH:11]2[CH2:10][NH:9][CH2:8]3)=[CH:3][CH:2]=1.[CH:14]1([C:17](Cl)=[O:18])[CH2:16][CH2:15]1>>[CH:14]1([C:17]([N:9]2[CH2:10][CH:11]3[C:7]([C:4]4[CH:3]=[CH:2][C:1]([CH3:13])=[CH:6][CH:5]=4)([CH2:12]3)[CH2:8]2)=[O:18])[CH2:16][CH2:15]1

Participants

Reactant 2

HCID 47953Bicifadine

HCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 128913693-Cyclopropanecarbonyl-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane

Procedure

In a like manner 1-(p-tolyl)-3-azabicyclo[3.1.0]hexane (Example 36) is reacted with cyclopropanecarbonyl chloride to give 3-cyclopropanecarbonyl-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane which is reduced as above to give 3-cyclopropylmethyl-1-(p-tolyl)-3-azabicyclo[3.1.0]hexane hydrochloride as colorless crystals, m.p. 180-182° C.

Sources & evidence

ORD record: ord-5a1eff1e00ab41e7a51b9803af8d9596
Source dataset: uspto-grants-1978_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04131611

Reaction notes

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