Hydrazine hydrate (1:1) → 4-(1-Diphenylmethylpiperidine-4-yl)butylamine

HRID 1280782Notes

Reaction equation

HRID 1280782 reaction equation
[C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]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:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[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 184257192-[4-(1-Diphenylmethylpiperidin-4-yl)-butyl]-isoindol-1,3-dione

Product 1

HCID 110346354-(1-Diphenylmethylpiperidine-4-yl)butylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

88.9 g (196 mmol) 2-[4-(1-diphenylmethylpiperidin-4-yl)-butyl]-isoindol-1,3-dione are suspended in 1000 ml ethanol and added to 22.0 g (440 mmol) hydrazine hydrate and heated to boiling for four hours. After cooling, the mixture is filtered and the solvent is removed under vacuum. The solid residue is distributed together with the filter residue under heat between 300 ml 10% sodium hydroxide solution and 300 ml acetic acid ethyl ester. The aqueous phase is extracted once again with 150 ml warm acetic acid ethyl ester. The combined organic phases are extracted twice, each with 300 ml 10% hydrochloric acid. The combined aqueous phases are adjusted to alkaline with 10% sodium hydroxide solution and extracted twice, each with 400 ml acetic acid ethyl ester. The combined organic phases are washed with 100 ml water and dried over sodium sulfate. The solvent is removed under vacuum, the residue is dried under high-vacuum and further processed without additional purification. Yield of gradually solidifying resin: 63 g (99%).

Workup

  1. temperatureheated
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. customthe solvent is removed under vacuum
  5. temperatureunder heat between 300 ml 10% sodium hydroxide solution and 300 ml acetic acid ethyl ester
  6. extractionThe aqueous phase is extracted once again with 150 ml
  7. temperaturewarm acetic acid ethyl ester
  8. extractionThe combined organic phases are extracted twice
  9. extractionextracted twice
  10. washThe combined organic phases are washed with 100 ml water
  11. dry with materialdried over sodium sulfate
  12. customThe solvent is removed under vacuum
  13. customthe residue is dried under high-vacuum
  14. customfurther processed without additional purification

Sources & evidence

ORD record
ord-95c001213042465d9ad4b36c258b6f96
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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