Chloroacetyl chloride → 1-{4-[N-(2-isopropyloxyethyl)-N-chloroacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine

HRID 1975352Notes

Reaction equation

HRID 1975352 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[CH:30]=[CH:29][C:11]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:16][CH2:15]2)=[O:13])=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[Cl:31][CH2:32][C:33](Cl)=[O:34]>C(Cl)Cl>[CH:1]([O:4][CH2:5][CH2:6][N:7]([C:8]1[CH:30]=[CH:29][C:11]([C:12]([N:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[CH2:18][CH2:19]2)=[O:13])=[CH:10][CH:9]=1)[C:33](=[O:34])[CH2:32][Cl:31])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 98455471-[4-(2-Isopropyloxyethyl)aminobenzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine

Product 1

HCID 98073911-{4-[N-(2-isopropyloxyethyl)-N-chloroacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner analogous to that described in Example 6, the oily 1-{4-[N-(2-isopropyloxyethyl)-N-chloroacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine is prepared from 1.35 g of 1-[4-(2-isopropyloxyethyl)aminobenzoyl]-4-[2-(4-chlorophenyl)ethyl]piperazine by reaction with chloroacetyl chloride; IR (CH2Cl2): 1650 cm-1 (broad); NMR (CDCl3): 1.15 (t, 3H), 1.8 (m, 2H), 2.5 (m) and 2.6 (t) (together 6H), 2.8 (t, 2H), 3.4 (m, 6H), 3.85 (m, 6H), 7.15 (d, 2H), 7.3 (m, 4H), 7.5 ppm (d, 2H).

Sources & evidence

ORD record
ord-ae4ea223c2aa4ada9d1ab7b5f4f69052
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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