N-(4-Bromophenyl)-2-chloroacetamide → N-(4-bromophenyl)-2-(pyrrolidin-1-yl)acetamide

HRID 1387051Notes

Reaction equation

HRID 1387051 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10]Cl)=[CH:4][CH:3]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:12])[CH2:10][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 17374N-(4-Bromophenyl)-2-chloroacetamideHCID 31268Pyrrolidine

Product 1

HCID 1091709N-(4-bromophenyl)-2-(pyrrolidin-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.0 g (0.02 mol) of N-(4-bromophenyl)-α-chloroacetamide (Part A) and 5.05 mL (0.06 mol) of pyrrolidine in 100 mL of THF was stirred overnight at ambient temperature. The mixture was concentrated in vacuo and the residue was partitioned between H2O and EtOAc. The organic layer was separated, washed with H2O, dried over Na2SO4, filtered, and evaporated in vacuo to afford 5.74 g of analytically pure title compound as crystals.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between H2O and EtOAc
  3. customThe organic layer was separated
  4. washwashed with H2O
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-846bec2310514558b4c8c7ac7758e998
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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