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

HRID 428847Notes

Reaction equation

HRID 428847 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:29](Cl)(=[O:31])=[O:30])[CH3:28]>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:29]([CH2:27][CH3:28])(=[O:31])=[O:30])[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 11667Ethanesulfonyl chlorideHCID 221413223-(3-Hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine

Product 1

HCID 22141238N-[3-(3-Hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]-1-ethanesulfonamideYield 52.3%

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 ethanesulfonylchloride (0.131 ml, 177 mg, 1.38 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 (140 mg, 52%).

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-a3f413b799e64bd3b3b318254df42b5b
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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