Pyridine → N-[3-(3-Hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]-1-propanesulfonamide

HRID 428848Notes

Reaction equation

HRID 428848 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].N1C=CC=CC=1.[CH2:27]([S:30](Cl)(=[O:32])=[O:31])[CH2:28][CH3:29]>ClCCl>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([NH:20][S:30]([CH2:27][CH2:28][CH3:29])(=[O:32])=[O:31])[CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 662791-Propanesulfonyl chlorideHCID 221413223-(3-Hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine

Product 1

HCID 22141305N-[3-(3-Hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]-1-propanesulfonamideYield 14.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine (Preparation 12, 200 mg, 0.735 mmol), in dichloromethane (5 ml) at room temperature was added pyridine (0.15 ml, 1.84 mmol) then dropwise over 5 minutes propane-sulfonylchloride (0.16 ml, 202 mg, 1.42 mmol). The mixture was stirred for 48 hours, concentrated in vacuo and the residue was purified by silica (10 g) column chromatography eluting with ethyl acetate then 90:10:1 ethyl acetate:methanol:ammonia solution (0.880). Product-containing fractions were combined and concentrated in vacuo to give the title compound as a pale yellow oil (40 mg, 14%).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by silica (10 g) column chromatography
  3. washeluting with ethyl acetate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c05380ce2a67480f8e51e49705e1c10f
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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