Dichloromethane → HCID 23001040, compound

HRID 397712Notes

Reaction equation

HRID 397712 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].ClCCl>N1C=CC=CC=1>[NH3:1].[CH2:14]([N:11]1[CH2:12][CH2:13][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:24]([CH3:23])(=[O:26])=[O:25])[CH:3]=2)([CH2:20][CH2:21][CH3:22])[CH2:9][CH2:10]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 23000976HCID 23000976, compound

Product 2

HCID 222AmmoniaHCID 23001040HCID 23001040, compoundYield 183.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(3-aminophenyl)-N-hexyl-4-n-propylpiperidine (Preparation 70, 25 mg, 0.08 mmol) in pyridine (0.5 ml) under nitrogen was added methanesulfonyl chloride (10 ml, 0.124 mmol) and the resultant mixture was stirred overnight. Ice (2 g) was added and, after 15 min, dichloromethane (3 ml) was added and the biphasic mixture was left to stir for 15 min. The layers were separated and the aqueous layer was extracted with dichloromethane (3 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by silica (5 g) column chromatography eluting with ethyl acetate:hexane:0.880 ammonia (60:40:1 to 80:20:1) to give the title compound as a colourless oil (28 mg, 92%). The free base was dissolved in diethyl ether (3 ml) and 1.1 mol equivalents of 1N ethereal hydrogen chloride solution was added to provide a precipitate. The solvent was decanted and the solid dried in vacuo to yield the title compound as a hygroscopic solid.

Workup

  1. waitthe biphasic mixture was left
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (3 ml)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThis was purified by silica (5 g) column chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-658eb642ac294af2bd6247a900ccbcc2
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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