Potassium Carbonate → N-(4-bromophenyl)-2-(pyrrolidin-1-yl)acetamide

HRID 2384941Notes

Reaction equation

HRID 2384941 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:23])[CH2:21]Cl)=[CH:15][CH:14]=1>C(#N)C.C(Cl)Cl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:23])[CH2:21][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 17374N-(4-Bromophenyl)-2-chloroacetamideHCID 31268Pyrrolidine

Product 1

HCID 1091709N-(4-bromophenyl)-2-(pyrrolidin-1-yl)acetamideYield 99.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Add potassium carbonate (2.1 g, 15.5 mmol) and pyrrolidine (9.65 mL, 116 mmol) to a solution of N-(4-bromophenyl)-2-chloroacetamide (2.0 g, 7.7 mmol) in acetonitrile (78 mL) at RT. Heat the mixture at 80° C. for 4 h. Cool the mixture to RT, dilute with CH2Cl2, and wash with brine and water. Dry the organic layer over Na2SO4, filter, and concentrate to give 2.17 g (99%) of the title compound. LC-ES/MS m/z (79Br) 283.0 [M+H]+.

Workup

  1. temperatureCool the mixture to RT
  2. washwash with brine and water
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-329036b9e1724bee98bc66b081f553f9
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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