Formic Acid → 101477-46-7

HRID 977918Notes

Reaction equation

HRID 977918 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:32]=[CH:31][C:17]([CH:18]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=1.C(O)=O.[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]/[C:39]([OH:41])=[O:40]>C(O)C>[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]/[C:39]([OH:41])=[O:40].[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:28]1[CH2:27][CH2:26][N:25]([CH:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:17]2[CH:16]=[CH:15][C:14]([F:13])=[CH:32][CH:31]=2)[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 691752,4-DimethoxybenzaldehydeHCID 444972Fumaric AcidHCID 27789901-[(4-fluorophenyl)(phenyl)methyl]piperazine

Product 1

HCID 6447833101477-46-7Yield 30.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,4-Dimethoxybenzaldehyde (6.65 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 for 1 hour under heat, and then 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 6.5 g (yield 30.4%) of 1-(2,4-dimethoxybenzyl)-4-(4-fluorobenzhydryl)piperazine fumarate as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-985197c93a8d472cb1a3aed43da32666
Source dataset
uspto-grants-1987_05
Patent number
US04663325

Reaction notes

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