Benzoyl chloride, 3-bromo- → 3-bromo-N-(1-cyclohexyl-3-pyrrolidinyl)benzamide

HRID 1659149Notes

Reaction equation

HRID 1659149 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:3]1.[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18]>C(Cl)(Cl)Cl>[CH:7]1([N:4]2[CH2:5][CH2:6][CH:2]([NH:1][C:17](=[O:18])[C:16]3[CH:20]=[CH:21][CH:22]=[C:14]([Br:13])[CH:15]=3)[CH2:3]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 74377Benzoyl chloride, 3-bromo-HCID 36700741-Cyclohexylpyrrolidin-3-amine

Product 1

HCID 215273213-bromo-N-(1-cyclohexyl-3-pyrrolidinyl)benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 16.2 g. (0.1 mole) of 3-amino-1-cyclohexylpyrrolidine in 100 ml. of chloroform was added with stirring 15.1 g. (0.07 mole) of 3-bromobenzoyl chloride. After stirring for one hour, the solution was extracted with dilute sodium hydroxide. The chloroform layer was dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized twice from ethyl acetate-isopropyl ether. The impure crystalline material was then partitioned between ethyl acetate and dilute hydrochloric acid. The acid layer was made basic with sodium hydroxide and extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate, concentrated, and the residue recrystallized from ethyl acetate-isopropyl ether solvent. The yield was 9.1 g. (36.6%); m.p. 128°-130°C.

Workup

  1. stirringAfter stirring for one hour
  2. extractionthe solution was extracted with dilute sodium hydroxide
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized twice from ethyl acetate-isopropyl ether
  6. customThe impure crystalline material was then partitioned between ethyl acetate and dilute hydrochloric acid
  7. extractionextracted with chloroform
  8. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customthe residue recrystallized from ethyl acetate-isopropyl ether solvent

Sources & evidence

ORD record
ord-d5eb618ff6114ccf9755d158b8c96d4d
Source dataset
uspto-grants-1976_06
Patent number
US03966957

Reaction notes

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