Sodium Hydroxide → 1-(1-Benzyl-4-piperidinyl)-3-methylcarbostyril hydrochloride

HRID 1648547Notes

Reaction equation

[Cl-:1].[Al+3].[Cl-].[Cl-].[CH3:5][C:6](=[CH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:7]([N:9]([CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)C1C=CC=CC=1)=[O:8].[OH-].[Na+]>ClC1C=CC=CC=1>[ClH:1].[CH2:22]([N:19]1[CH2:18][CH2:17][CH:16]([N:9]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[C:6]([CH3:5])[C:7]2=[O:8])[CH2:21][CH2:20]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To grinded aluminum chloride (26 g) are added chlorobenzene (26 ml) and N-(α-methylcinnamoyl)-N-(1-benzyl-4-piperidinyl)aniline (8.7 g) and the mixture is heated at 110° C. for 1 hour. After cooling, the reaction mixture is poured into ice-water and made alkaline with an aqueous sodium hydroxide solution. After extraction with dichloromethane, the extract is concentrated and the resulting residue is purified by silica gel column chromatography (eluent; methylene chloride). The purified substance is converted into hydrochloride and then recrystallized from ethanol/water to give 1-(1-benzyl-4-piperidinyl)-3-methylcarbostyril hydrochloride (5.8 g) as colorless needles, m.p. 274°-276° C.

Workup

temperatureAfter cooling
extractionAfter extraction with dichloromethane
concentrationthe extract is concentrated
customthe resulting residue is purified by silica gel column chromatography (eluent; methylene chloride)
customrecrystallized from ethanol/water

Sources & evidence

ORD record: ord-93b93f7de06f401c86f22ea800918403
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05436254

Reaction notes

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