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

HRID 1667102Notes

Reaction equation

HRID 1667102 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[O:15]=[C:16]1[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:18][N:17]1[CH2:33][C:34](O)=[O:35].C(N(C(C)C)CC)(C)C>ClCCl>[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:34](=[O:35])[CH2:33][N:17]3[CH2:18][CH2:19][C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:16]3=[O:15])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7965631-(4-Fluorobenzyl)piperazineHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 574037811-{2-[4-(4-Fluorobenzyl)piperazin-1-yl]-2-oxoethyl}-3,3-diphenylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(4-fluorobenzyl)piperazine (0.081 g, 0.416 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.165 g, 0.436 mmol) and 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.135 g, 0.457 mmol) in dichloromethane (1 mL) was added diisopropylethylamine (0.109 mL, 0.623 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was concentrated and loaded onto a silica gel column (Analogix® SF25-25) and eluted with a gradient of 5% to 100% ethyl acetate/hexanes to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.20-7.37 (m, 12H), 6.97-7.04 (m, 2H), 4.18 (s, 2H), 3.59 (t, J=4.7 Hz, 2H), 3.51 (t, J=6.5 Hz, 2H), 3.44 (s, 2H), 3.39-3.44 (m, 2H), 2.81 (t, J=6.5 Hz, 2H), 2.38 (t, J=4.9 Hz, 2H), 2.28-2.32 (m, 2H); MS (ESI+) m/z 472 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. washeluted with a gradient of 5% to 100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1731991f7bc54b9d98d809b16656242d
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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