Hydrazine hydrate (1:1) → 2-[1-(4-Fluorobenzyl)piperidin-4-yl]ethylamine

HRID 54549Notes

Reaction equation

HRID 54549 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][N:15]3C(=O)C4=CC=CC=C4C3=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.O.NN>C(O)C>[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][NH2:15])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19959203N-[2-[1-(4-fluorobenzyl)piperidin-4-yl]ethyl]phthalimide

Product 1

HCID 172215202-[1-(4-Fluorobenzyl)piperidin-4-yl]ethylamineYield 54.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[2-[1-(4-fluorobenzyl)piperidin-4-yl]ethyl]phthalimide (12.7 g) and hydrazine hydrate (2.02 ml) in ethanol (150 ml) was refluxed for 2 hours. After cooling to room temperature, the mixture was evaporated in vacuo. The residue was chromatographed on alumina eluting with chloroform and the fractions containing the object product were collected and evaporated to give 2-[1-(4-fluorobenzyl)piperidin-4-yl]ethylamine (4.5 g) as an oil.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customthe mixture was evaporated in vacuo
  3. customThe residue was chromatographed on alumina eluting with chloroform
  4. additionthe fractions containing the object product
  5. customwere collected
  6. customevaporated

Sources & evidence

ORD record
ord-044df5bc6f08462591cced3bf193f968
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

Loading…