(4-Chlorophenyl)[1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]methanone → 3-(p-Chlorobenzyl)-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane

HRID 66278Notes

Reaction equation

HRID 66278 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[CH2:13][CH:12]3[C:10]([C:14]4[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=4)([CH2:11]3)[CH2:9]2)=O)=[CH:4][CH:3]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:8]2[CH2:13][CH:12]3[C:10]([C:14]4[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=4)([CH2:11]3)[CH2:9]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 20468348(4-Chlorophenyl)[1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]methanoneHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 132790213-(p-Chlorobenzyl)-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 16.60 g portion of 3-(p-chlorobenzoyl)-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane (prepared above) is dissolved in 160 ml of benzene and 55.5 g of sodium bis(2-methoxyethoxy)aluminum hydride (70% benzene solution) is added dropwise. The mixture is refluxed for 2 hours, cooled and quenched slowly with 10N sodium hydroxide. Water is added, the organic layer is separated and washed 3 times with water and then dried over sodium magnesium sulfate. Removal of the solvent yields an off-white solid, mp 88°-92° C.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. temperaturecooled
  3. customquenched slowly with 10N sodium hydroxide
  4. additionWater is added
  5. customthe organic layer is separated
  6. washwashed 3 times with water
  7. dry with materialdried over sodium magnesium sulfate
  8. customRemoval of the solvent
  9. customyields an off-white solid, mp 88°-92° C.

Sources & evidence

ORD record
ord-957e0430f0bb4036ad303bbdd4622c04
Source dataset
uspto-grants-1978_12
Patent number
US04131611

Reaction notes

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