1-(2,4-Dichlorobenzyl)piperazine → 1-{2-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpyrrolidin-2-one

HRID 1667104Notes

Reaction equation

HRID 1667104 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[O:13]=[C:14]1[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15]1[CH2:31][C:32](O)=[O:33].[Cl:35][C:36]1[CH:48]=[C:47]([Cl:49])[CH:46]=[CH:45][C:37]=1[CH2:38][N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>ClCCl>[Cl:35][C:36]1[CH:48]=[C:47]([Cl:49])[CH:46]=[CH:45][C:37]=1[CH2:38][N:39]1[CH2:40][CH2:41][N:42]([C:32](=[O:33])[CH2:31][N:15]2[CH2:16][CH2:17][C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:14]2=[O:13])[CH2:43][CH2:44]1

Participants

5

Reactant 3

HCID 4111791-(2,4-Dichlorobenzyl)piperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 573968151-{2-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.049 g, 0.254 mmol), 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.050 g, 0.169 mmol) and 1-(2,4-dichlorobenzyl)piperazine (0.046 g, 0.186 mmol) in dichloromethane (0.5 mL) was stirred at room temperature. After stirring overnight, the reaction was loaded directly onto a SF15-12 silica gel column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.20-7.39 (m, 13H), 4.19 (s, 2H), 3.59 (t, J=4.8 Hz, 2H), 3.53 (s, 2H), 3.52 (t, J=6.4 Hz, 2H), 3.42 (t, J=4.9 Hz, 2H), 2.81 (t, J=6.5 Hz, 2H), 2.43 (t, J=4.9 Hz, 2H), 2.32 (t, J=4.9 Hz, 2H); MS (ESI+) m/z 522 (M+H)+.

Workup

  1. stirringAfter stirring overnight
  2. washthe title compound was eluted
  3. customover 20 minutes

Sources & evidence

ORD record
ord-b88c0d9f1ea64c9a97b81ad7e7874b52
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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