Ethanesulfonyl chloride → HCID 9929680, compound

HRID 1826338Notes

Reaction equation

HRID 1826338 reaction equation
[CH2:1]([C:3]1([C:18]2[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=2)[CH:8]2[CH:4]1[CH2:5][N:6]([CH2:9][CH2:10][CH2:11][C:12]1C=CC=[CH:14][CH:13]=1)[CH2:7]2)[CH3:2].[CH2:25]([S:27](Cl)(=[O:29])=[O:28])[CH3:26]>N1C=CC=CC=1>[CH2:1]([C:3]1([C:18]2[CH:19]=[C:20]([NH:24][S:27]([CH2:25][CH3:26])(=[O:29])=[O:28])[CH:21]=[CH:22][CH:23]=2)[CH:8]2[CH:4]1[CH2:5][N:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7]2)[CH3:2]

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 22141186HCID 22141186, compound

Product 1

HCID 9929680HCID 9929680, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-[6-ethyl-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine (Preparation 20, 500 mg, 1.56 mmol) in pyridine (5 ml), at 0° C. under nitrogen was added dropwise over 5 minutes ethanesulfonylchloride (0.25 ml, 0.34 g, 2.6 mmol). The mixture was allowed to warm to room temperature and was stirred for 18 hours. The mixture was concentrated in vacuo and the residue was purified by silica (25 g) column chromatography eluting with 50:50:1 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 (150 mg, 31%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica (25 g) column chromatography
  3. washeluting with 50:50:1 ethyl acetate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-025166a722a240178985de0d56f56a51
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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