Formic Acid → Lomerizine Hydrochloride

HRID 977921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977921
[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:21]=[CH:20][C:19]([CH:22]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1.C(O)=O.[ClH:39]>C(O)C>[ClH:39].[ClH:39].[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:33]1[CH2:32][CH2:31][N:30]([CH:22]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=2)[CH2:35][CH2:34]1

Komponenten

6

Edukt 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 750062,3,4-TrimethoxybenzaldehydeHCID 1529321-(Bis(4-fluorophenyl)methyl)piperazine

Produkt 1

HCID 122125Lomerizine HydrochlorideAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2,3,4-Trimethoxybenzaldehyde (42.1 g; 215 millimoles) and 61.9 g (215 millimoles) of bis(4-fluorophenyl)methylpiperazine were melted in an oil bath at 100° C., and 10 ml (265 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 40 ml of conc. hydrochloric acid and 400 ml of ethanol was added, and the mixture was concentrated under reduced pressure. Ether was added, and the precipitated crystals were collected by filtration. Recrystallization of the crystals from ethanol-ether gave 55.5 g (yield 47.7%) of 1-(2,3,4-trimethoxybenzyl)-4-[bis(4-fluorophenyl)methyl]piperazine dihydrochloride as colorless crystals.

Aufarbeitung

  1. temperatureunder heat for 30 minutes
  2. additionwas added
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionEther was added
  5. filtrationthe precipitated crystals were collected by filtration
  6. customRecrystallization of the crystals from ethanol-ether

Quellen und Nachweise

ORD-Eintrag
ord-530cddefaa1945238366be1bc1146287
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04663325

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