Ethanol → HCID 20311665, compound

HRID 2420472Notes

Reaction equation

HRID 2420472 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][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(O)C.[C:22]1([C:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:29][CH:30]=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH4-].[Na+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([CH2:13][CH:14]([NH:15][CH2:30][CH:29]=[C:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH3:16])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 710273,3-DiphenylacroleinHCID 4311764Sodium borohydrideHCID 20311667HCID 20311667, compound

Product 1

HCID 20311665HCID 20311665, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: The mixture of 12.1 g of dl-4-(2-pyridylmethoxy)-amphetamine, 400 ml of absolute ethanol and 10.4 g of β-phenylcinnamaldehyde is treated dropwise under stirring with the solution of 3.5 g of sodium borohydride in 10 ml of water. The whole is then stirred and refluxed overnight, concentrated and the concentrate diluted with water. It is extracted with ethyl acetate, the organic layer washed with saturated aqueous sodium chloride, dried and evaporated to yield the dl-1-[4-(2-pyridylmethoxy)-phenyl]-2-(3,3-diphenylallylamino)-propane.

Workup

  1. customThe starting material is prepared
  2. additionis treated dropwise
  3. temperaturerefluxed overnight
  4. concentrationconcentrated
  5. additionthe concentrate diluted with water
  6. extractionIt is extracted with ethyl acetate
  7. washthe organic layer washed with saturated aqueous sodium chloride
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-9a45554ec1bb46d288193e2b2cce42ec
Source dataset
uspto-grants-1978_08
Patent number
US04110457

Reaction notes

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