Water → HCID 22141139, compound

HRID 428851Notes

Reaction equation

HRID 428851 reaction equation
[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6]2.[CH2:24]([S:27](Cl)(=[O:29])=[O:28])[CH2:25][CH3:26].[OH2:31]>ClCCl>[C:21]([OH:28])(=[O:31])[CH3:22].[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:27]([CH2:24][CH2:25][CH3:26])(=[O:29])=[O:28])[CH:20]=[CH:21][CH:22]=2)[CH:3]2[CH:7]1[CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4]2

Participants

5

Reactant 3

HCID 962WaterHCID 662791-Propanesulfonyl chlorideHCID 11266768HCID 11266768, compound

Product 1

HCID 22141139HCID 22141139, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[6-methyl-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine (Preparation 8, 200 mg, 0.65 mmol) in pynidine (2 ml) under nitrogen at 0° C. was added n-propanesulfonyl chloride (140 mg, 0.98 mmol), then the mixture was stirred at room temperature for 16 hours. Water (5 ml) and dichloromethane (5 ml) were added, and the mixture was stirred for 30 minutes. The organic phase was washed further with water (5 ml) for 30 minutes, separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica (10 g) column chromatography eluting with ethyl acetate:hexane:ammonia solution (0.880) (20:80:1 then 50:50:1). Product-containing fractions were combined and concentrated in vacuo. The residue was further purified by preparative HPLC (condition 4). Combination and evaporation of appropriate fractions gave the title compound as a pale brown solid (11 mg, 4%).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. washThe organic phase was washed further with water (5 ml) for 30 minutes
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica (10 g) column chromatography
  8. washeluting with ethyl acetate
  9. concentrationconcentrated in vacuo
  10. customThe residue was further purified by preparative HPLC (condition 4)
  11. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-a2c7ede328c142acb416f861f018cfd9
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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