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

HRID 236750
Notes
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Reaction equation

HRID 236750 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 3017393Ethyl 4-[(4-chlorophenyl)(phenylacetyl)amino]piperidine-1-carboxylate

Product 1

HCID 19829426N-(4-chlorophenyl)-N-(4-piperidinyl)benzeneacetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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 9h. 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

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

Sources & evidence

ORD record
ord-db616cc462204ef99152ae02cda17c37
Source dataset
uspto-grants-1979_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04157393

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes