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Acetoxyacetyl chloride → 1-[4-(2-Isopropyloxyethyl)aminobenzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine

HRID 1975366
Notes
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Reaction equation

HRID 1975366 reaction equation
Cl.[CH:2]([O:5][CH2:6][CH2:7][N:8]([C:16]1[CH:38]=[CH:37][C:19]([C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1)C(=O)COC(=O)C)([CH3:4])[CH3:3].C(OCC(Cl)=O)(=O)C>>[CH:2]([O:5][CH2:6][CH2:7][NH:8][C:16]1[CH:38]=[CH:37][C:19]([C:20]([N:22]2[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[CH2:26][CH2:27]2)=[O:21])=[CH:18][CH:17]=1)([CH3:4])[CH3:3]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 190994951-{4-[N-(2-isopropyloxyethyl)-N-acetoxyacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride

Product 1

HCID 98455471-[4-(2-Isopropyloxyethyl)aminobenzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine

Procedure

In a manner analogous to that described in Example 23, 1-{4-[N-(2-isopropyloxyethyl)-N-acetoxyacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine hydrochloride having a melting point of 130°-132° is obtained from 5 g of 1-{4-[N-(2-isopropyloxyethyl)amino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine (Example 21) by reaction with acetoxyacetic acid chloride.

Sources & evidence

ORD record
ord-c9670a2fe71942ee9844feae60c5860c
Source dataset
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05286728

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes