Ethanol → 4-[4-(Diphenylmethylidene)piperidin-1-yl]butan-1-amine

HRID 1089125Notes

Reaction equation

HRID 1089125 reaction equation
[C:1]1([C:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3C(=O)C4=CC=CC=C4C3=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN.C(O)C>O>[C:1]1([C:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 15096000N-[4-(4-diphenylmethylene-1-piperidyl)butyl]phthalimide

Product 1

HCID 156165494-[4-(Diphenylmethylidene)piperidin-1-yl]butan-1-amineYield 123.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The obtained phthalimide compound (13.7 g) and hydrazine monohydrate (2.5 g) are added to ethanol (34 ml) and the mixture is refluxed with stirring for 2 hours. After cooling, a small amount of water is added to the reaction mixture and the solvent is distilled off under reduced pressure. Chloroform (200 ml) is added to the residue and the insoluble substances are filtered off and washed twice with chloroform (each 50 ml). The filtrate and the washings are combined together, washed with water, dried over anhydrous magnesium sulfate and concentrated to give the desired compound (12 g). Mass spectrum m/z: 320 (M+)

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. distillationthe solvent is distilled off under reduced pressure
  4. additionChloroform (200 ml) is added to the residue
  5. filtrationthe insoluble substances are filtered off
  6. washwashed twice with chloroform (each 50 ml)
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f329b6ed778d4d788dc14baadbe47f5b
Source dataset
uspto-grants-1990_10
Patent number
US04965266

Reaction notes

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