Formic Acid → 101477-51-4

HRID 977920Notes

Reaction equation

HRID 977920 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[F:15][C:16]1[CH:34]=[CH:33][C:19]([CH:20]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][CH:17]=1.C(O)=O.[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42]>C(O)C>[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42].[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH2:5][N:30]1[CH2:29][CH2:28][N:27]([CH:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:34][CH:33]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 750062,3,4-TrimethoxybenzaldehydeHCID 444972Fumaric AcidHCID 27789901-[(4-fluorophenyl)(phenyl)methyl]piperazine

Product 1

HCID 6447834101477-51-4Yield 32.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,3,4-Trimethoxybenzaldehyde (7.85 g; 40.0 millimoles) and 10.8 g (39.9 millimoles) of 4-fluorobenzhydrylpiperazine (see German OLS 1929330) were melted in an oil bath at 120° C., and 2.3 ml (61.0 millimoles) of formic acid was added dropwise. The mixture was stirred under heat for 1 hour, and allowed to cool to room temperature. Then, 50 ml of an ethanol solution containing 5.0 g (43.1 millimoles) of fumaric acid was added, and the precipitated crystals were collected by filtration. Recrystallization of the crystals from ethanol gave 7.4 g (yield 32.7%) of 1-(2,3,4-trimethoxybenzyl)-4-(4-fluorobenzhydryl)piperazine fumarate as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-88608b345fa54131849fc66348e05090
Source dataset
uspto-grants-1987_05
Patent number
US04663325

Reaction notes

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