Hydrazine hydrate (1:1) → 3-(1-Diphenylmethylpiperidine-4-yl)-propylamine

HRID 1280779Notes

Reaction equation

HRID 1280779 reaction equation
[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][N:17]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>C(O)C>[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 184257262-[3-(1-Diphenylmethylpiperidine-4-yl)-propyl]-isoindol-1,3-dione

Product 1

HCID 184257323-(1-Diphenylmethylpiperidine-4-yl)-propylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.8 g (29.2 mmol) 2-[3-(1-diphenylmethylpiperidine-4-yl)-propyl]-isoindol-1,3-dione are suspended in 110 ml ethanol and added to 2.2 ml (58.4 mmol) hydrazine hydrate and heated to boiling for three hours. After cooling, the mixture is concentrated under vacuum. The residue is dispersed between 300 ml dichloromethane and 50 ml 10% sodium hydroxide solution. The aqueous phase is extracted twice, each with 200 ml dichloromethane. The combined organic phases are washed twice, each with 20 ml water, and dried over sodium sulfate. The solvent is removed under vacuum and the residue is processed fruther without additional purification. Yield 7.3 g (81%)

Workup

  1. temperatureheated
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated under vacuum
  4. additionThe residue is dispersed between 300 ml dichloromethane and 50 ml 10% sodium hydroxide solution
  5. extractionThe aqueous phase is extracted twice
  6. washThe combined organic phases are washed twice
  7. dry with materialeach with 20 ml water, and dried over sodium sulfate
  8. customThe solvent is removed under vacuum
  9. customwithout additional purification

Sources & evidence

ORD record
ord-0b661ec4c00b4166a7987263b5746957
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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