3,3-Diphenylacrolein → HCID 13065282, compound

HRID 1065474Notes

Reaction equation

HRID 1065474 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([CH2:13][CH:14]([CH3:16])[NH2:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:26][CH:27]=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][CH:14]([NH:15][CH2:27][CH:26]=[C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH3:16])=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 710273,3-DiphenylacroleinHCID 1346161-[4-(Benzyloxy)phenyl]propan-2-amineHCID 4311764Sodium borohydride

Product 1

HCID 13065282HCID 13065282, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The starting material is prepared as follows: The solution of 12 g of dl-p-benzyloxyamphetamine, and 10.4 g of β-phenyl-cinnamaldehyde in 300 ml of absolute ethanol is treated dropwse with the solution of 3 g of sodium borohydride in 6.7 ml of water while stirring. It is refluxed for 18 hours, concentrated to remove most of the ethanol and diluted with water. The mixture is extracted with ethyl acetate and the organic layer washed with brine, dried and evaporated, to yield the dl-1-(p-benzyloxyphenyl)-2-(3,3-diphenylallylamino)-propane; its maleate melts at 177°-178°.

Workup

  1. customThe starting material is prepared
  2. temperatureIt is refluxed for 18 hours
  3. concentrationconcentrated
  4. customto remove most of the ethanol
  5. additiondiluted with water
  6. extractionThe mixture is extracted with ethyl acetate
  7. washthe organic layer washed with brine
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-dec3d6f7cac04e4aad5cf5116fca34f3
Source dataset
uspto-grants-1982_05
Patent number
US04329367

Reaction notes

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