Diisopropylethylamine → 1-{2-[4-(2,6-Dichlorobenzyl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpyrrolidin-2-one

HRID 1667100Notes

Reaction equation

HRID 1667100 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[O:16]=[C:17]1[C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][CH2:19][N:18]1[CH2:34][C:35](O)=[O:36].C(N(C(C)C)CC)(C)C>ClCCl>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][N:8]([C:35](=[O:36])[CH2:34][N:18]2[CH2:19][CH2:20][C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]2=[O:16])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7707961-(2,6-Dichlorobenzyl)piperazineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 452743081-{2-[4-(2,6-Dichlorobenzyl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(2,6-dichlorobenzyl)piperazine (0.045 g, 0.183 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.069 g, 0.183 mmol) and 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.054 g, 0.183 mmol) in dichloromethane (0.5 mL) was added diisopropylethylamine (0.048 mL, 0.274 mmol), and the reaction mixture was stirred at room temperature. After stirring overnight, thin layer chromatography (hexanes/ethyl acetate 1:1) indicated formation of the product. 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 75% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.10-7.38 (m, 13H), 4.19 (s, 2H), 3.71 (s, 2H), 3.48-3.59 (m, 4H), 3.33-3.40 (m, 2H), 2.81 (t, J=6.5 Hz, 2H), 2.50-2.58 (m, 2H), 2.41-2.49 (m, 2H); MS (DCI+) m/z 522.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-217ff6814d7f4e15a45001770054099d
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…