Formic Acid → Piperazine, 1-(bis(4-fluorophenyl)methyl)-4-((2,4-dimethoxyphenyl)methyl)-, hydrochloride, hydrate (1:2:2)

HRID 977919Notes

Reaction equation

HRID 977919 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.C(O)=O.[ClH:37]>C(O)C>[ClH:37].[ClH:37].[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][N:31]1[CH2:30][CH2:29][N:28]([CH:20]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:17]2[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=2)[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 691752,4-DimethoxybenzaldehydeHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazine

Product 1

HCID 3063696Piperazine, 1-(bis(4-fluorophenyl)methyl)-4-((2,4-dimethoxyphenyl)methyl)-, hydrochloride, hydrate (1:2:2)Yield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dimethoxybenzaldehyde (6.7 g; 40.3 millimoles) and 11.5 g (39.9 millimoles) of bis(4-fluorophenyl)methylpiperazine were melted in an oil bath at 100° C., and 2.0 ml (53.0 millimoles) of formic acid was added dropwise. The mixture was stirred under heat for 30 minutes, and allowed to cool to room temperature. A mixture of 8 ml of conc. hydrochloric acid and 80 ml of ethanol was added, and the precipitated crystals were collected by filtration. Recrystallization of the crystals from ethanol gave 5.1 g (yield 25.0%) of 1-(2,4-dimethoxybenzyl)-4-[bis(4-fluorophenyl)methyl]piperazine dihydrochloride as colorless crystals.

Workup

  1. temperatureunder heat for 30 minutes
  2. additionwas added
  3. filtrationthe precipitated crystals were collected by filtration
  4. customRecrystallization of the crystals from ethanol

Sources & evidence

ORD record
ord-c54ca02d45fc4f7ba6d2e186ac882259
Source dataset
uspto-grants-1987_05
Patent number
US04663325

Reaction notes

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