Pyridine → N-[3-(3-{3-Phenylpropyl}-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide

HRID 428849Notes

Reaction equation

HRID 428849 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH:14]3[CH:12]([CH:13]3[C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH:12]3[CH:14]([CH:13]3[C:16]3[CH:17]=[C:18]([NH:22][S:30]([CH3:29])(=[O:32])=[O:31])[CH:19]=[CH:20][CH:21]=3)[CH2:15]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 221411543-[3-(3-Phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine

Product 1

HCID 22141129N-[3-(3-{3-Phenylpropyl}-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine (Preparation 25, 34 mg, 0.11 mmol) in dichloromethane (2 ml) at 0° C. under nitrogen was added pyridine (20 μl, 0.24 mmol) then methanesulfonylchloride (13 mg, 10 μl, 0.11 mmol). The mixture was allowed to warm to room temperature and was stirred for 1.5 hours. The mixture was concentrated in vacuo and the residue was purified by silica (5 g) column chromatography eluting with 80:20:1 ethyl acetate:hexane:ammonia solution (0.880). Product-containing fractions were combined and concentrated in vacuo to give the title compound as a pale yellow oil (29 mg, 71%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica (5 g) column chromatography
  3. washeluting with 80:20:1 ethyl acetate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acd589fc4b204c6db630fe79e1d9c665
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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