Red-Al → 3-(p-Chlorobenzyl)-1-(p-chlorophenyl)-3-azabicyclo[3.1.0]hexane

HRID 1903255Notes

Reaction equation

HRID 1903255 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.COCCO[AlH2-]OCCOC.[Na+]>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 16684438Red-AlHCID 20468348(4-Chlorophenyl)[1-(4-chlorophenyl)-3-azabicyclo[3.1.0]hexan-3-yl]methanone

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 is dissolved in 160 ml. of benzene and 55.5 g. of Vitride® is added dropwise. The mixture is refluxed for 2 hours, cooled and quenched slowly with 10 N sodium hydroxide. Water is added, the organic layer is separated and washed 3 times with water and then dried over magnesium sulfate. Removal of the solvent yields an off-white solid, m.p. 88°-92° C.

Workup

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

Sources & evidence

ORD record
ord-748a451e77d9495bb7be7fb378e3d541
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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