Ammonium formate → 1-[2-(2-Fluorophenyl)propyl]piperazine

HRID 1600839Notes

Reaction equation

HRID 1600839 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH3:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[Pd+2].[OH-]>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:15]([CH3:16])[CH2:14][N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 218308454-Benzyl-1-[2-(2-fluorophenyl)propyl]piperazine

Product 1

HCID 218308551-[2-(2-Fluorophenyl)propyl]piperazineYield 73.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

4-Benzyl-1-[2-(2-fluorophenyl)propyl]piperazine (3.17 g, 0.01 mol), ammonium formate (3.2 g, 0.05 mol) and palladium (II) hydroxide on carbon (10% w/w, 1.6 g) were mixed in methanol (200 ml) and heated under reflux for 18 h. The catalyst was filtered off through celite and the filtrate evaporated. Chromatography on silica gel with dichloromethane-methanol-880 ammonia (80:8:1) yielded 1-[2-(2-fluorophenyl)propyl]piperazine (1.64 g, 73%) as a colourless oil, δH (250 MHz, CDCl3) 1.2 (3H, d, J 7.0, Me), 2.3-2.6 (6H, m, CH2), 2.8-3.0 (4H, m, CH2), 3.1-3.2 (1H, m, MeCH), 6.9-7.4 (4H, m, ArH).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 h
  3. filtrationThe catalyst was filtered off through celite
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-f715653b0087414892490c7a14156728
Source dataset
uspto-grants-1999_11
Patent number
US05977116

Reaction notes

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