Hydrogen Bromide → N-(4-chlorophenyl)-N-(4-piperidinyl)benzeneacetamide hydrochloride

HRID 1706736Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:18]2[CH2:23][CH2:22][N:21](C(OCC)=O)[CH2:20][CH2:19]2)[C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.Br>C(O)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 62 °C

Procedure

A mixture of 10 parts of ethyl 4-[N-(4-chlorophenyl)-N-(phenylacetyl)amino]-1-piperidinecarboxylate and 125 parts of glacial acetic acid, previously saturated with gaseous hydrogen bromide, is heated for 9 h. 45 at 62° C., while stirring. The reaction mixture is cooled and glacial acetic acid is evaporated in vacuo. The semi-solid residue is taken up in 150 parts of water, alkalized with a concentrated sodium hydroxide solution and the product is extracted with trichloromethane. The extract is dried over sodium sulfate and evaporated. The oily residue is triturated in 56 parts of 1,1'-oxybisethane and the solid crude free base is filtered off. It is converted into the hydrochloride salt in the conventional manner in 1,1'-oxybisethane and 2-propanone, yielding 4 parts of N-(4-chlorophenyl)-N-(4-piperidinyl)benzeneacetamide hydrochloride; mp. 206.5° C.

Workup

temperatureThe reaction mixture is cooled
customglacial acetic acid is evaporated in vacuo
extractionthe product is extracted with trichloromethane
dry with materialThe extract is dried over sodium sulfate
customevaporated
customThe oily residue is triturated in 56 parts of 1,1'-oxybisethane
filtrationthe solid crude free base is filtered off

Sources & evidence

ORD record: ord-b63e0f2599c7459b9464d0b171c3650f
Source dataset: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04208418

Reaction notes

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