N-Cyclohexyl-2-pyrrolidone → 3-(4-Bromo-2-chlorobenzyl)-1-cyclohexylpyrrolidin-2-one

HRID 2235183Notes

Reaction equation

HRID 2235183 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28]Br)=[C:24]([Cl:30])[CH:23]=1>>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:9]2[CH2:10][CH2:11][N:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:8]2=[O:12])=[C:24]([Cl:30])[CH:23]=1

Participants

4

Reactant 3

HCID 81278N-Cyclohexyl-2-pyrrolidoneHCID 2724682Lithium diisopropylamideHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzene

Product 1

HCID 116822063-(4-Bromo-2-chlorobenzyl)-1-cyclohexylpyrrolidin-2-oneYield 66.2%

Procedure

Using the procedure to synthesize Example 1 and using reagents N-cyclohexylpyrrolidinone (15 g, 89.7 mmol), LDA (2.0 M, 53.8 mL, 107.6 mmol) and 4-bromo-1-bromomethyl-2-chloro-benzene (preparation 5) (30.6 mg, 107.6 mmol) affords 22 g (66%) of 3-(4-bromo-2-chloro-benzyl)-1-cyclohexyl-pyrrolidin-2-one.

Workup

  1. customto synthesize Example 1

Sources & evidence

ORD record
ord-89692a0728284591aa657e1e13934bb5
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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