Diiodomethane → Bicifadine

HRID 1903270Notes

Reaction equation

HRID 1903270 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([C:7]2[CH2:8][NH:9][CH2:10][CH:11]=2)=[CH:3][CH:2]=1.[CH2:13](I)I>C1C=CC=CC=1.[Cu]>[C:1]1([CH3:12])[CH:2]=[CH:3][C:4]([C:7]23[CH2:13][CH:11]2[CH2:10][NH:9][CH2:8]3)=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6346DiiodomethaneHCID 3024855HCID 3024855, compound

Product 1

HCID 47953Bicifadine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 3-(p-tolyl)-3-pyrroline, methylene iodide, and powdered copper in a molar ration of 1:2:4 is heated in benzene for about 50 hours. Filtration and evaporation of the solution gives 1-(p-tolyl)-3-azabicyclo[3.1.0]hexane.

Workup

  1. filtrationFiltration and evaporation of the solution

Sources & evidence

ORD record
ord-67f402ae0a6640d2b0a6e50f5d17463b
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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