Water → 1-(4-Methanesulphonylaminophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione

HRID 35085Notes

Reaction equation

HRID 35085 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]23[CH2:19][CH:17]([CH2:18]2)[C:16](=[O:20])[N:15]([CH2:21][CH2:22][CH3:23])[C:14]3=[O:24])=[CH:9][CH:8]=1.O>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][S:2]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]23[CH2:18][CH:17]([CH2:19]2)[C:16](=[O:20])[N:15]([CH2:21][CH2:22][CH3:23])[C:14]3=[O:24])=[CH:11][CH:12]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 148726221-(4-Amino-phenyl)-3-propyl-3-aza-bicyclo[3.1.1]heptane-2,4-dione

Product 1

HCID 200278361-(4-Methanesulphonylaminophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.31 ml of methanesulphonic acid chloride in 3 ml of methylene chloride is added at room temperature to a solution of 1.03 g of 1-(4-aminophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione and 24 mg of 4-dimethylaaminopyridine in 10 ml of pyridine. After stirring for 5 hours, 50 ml of water are added, and the mixture is left to stand overnight at 0°-5°. Extraction is carried out with methylene chloride, and the organic phase is washed in succession with water, cold 2N hydrochloric acid, water, semi-saturated bicarbonate solution and water. After drying over magnesium sulphate, the mixture is filtered and concentrated by evaporation, and the residue is recrystallised from methanol. The title compound is obtained in the form of white crystals having a melting point of 159°-160°. Rf (hexane/ethyl acetate 1:1)=0.15.

Workup

  1. waitthe mixture is left
  2. waitto stand overnight at 0°-5°
  3. extractionExtraction
  4. washthe organic phase is washed in succession with water, cold 2N hydrochloric acid, water, semi-saturated bicarbonate solution and water
  5. dry with materialAfter drying over magnesium sulphate
  6. filtrationthe mixture is filtered
  7. concentrationconcentrated by evaporation
  8. customthe residue is recrystallised from methanol

Sources & evidence

ORD record
ord-dab73a85ed0241b99c5dbb9c7a63b148
Source dataset
uspto-grants-1988_08
Patent number
US04764640

Reaction notes

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