Hydrazine → 1-[1-(2-Phenylethyl)piperidin-4-yl]methanamine

HRID 1708038Notes

Reaction equation

HRID 1708038 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][N:16]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN>C(O)C>[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH2:16])[CH2:11][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 54026502HCID 54026502, compound

Product 1

HCID 114586431-[1-(2-Phenylethyl)piperidin-4-yl]methanamineYield 108.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.31 g (3.8 mmoles ) of 2-[1-(2-phenylethyl)-4-piperidylmethyl]-1H-isoindole-1,3(2H)-dione (Example 2) and 0.25 mL (7.8 mmoles) of hydrazine in 20 mL of ethanol was heated under reflux for 4 hours. The solvent was removed and the residue was made basic with aqueous potassium hydroxide and extracted with chloroform to give 0.90 g of 1-(2-phenylethyl)-4-piperidinemethylamine as an oil. NMR (CDCl3): δ7.14-7.35 (m, 5H); 2.93-3.10 (d, 2H); 2.72-2.85 (m, 2H); 2.52-2.65 (m, 4H); 1.92-2.05 (t, 2H); 1.61-1.87 (m, 2H); 1.08-1.48 (m, 5H) .

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customThe solvent was removed
  4. extractionextracted with chloroform

Sources & evidence

ORD record
ord-b6d91173cf544e7d9af5d8981792693e
Source dataset
uspto-grants-1994_10
Patent number
US05356906

Reaction notes

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