Pyridine → HCID 54458887, compound

HRID 397709Notes

Reaction equation

HRID 397709 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:20])[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.[CH2:21]([S:24](Cl)(=[O:26])=[O:25])[CH2:22][CH3:23].N1C=CC=CC=1>ClCCl>[NH3:1].[CH2:14]([N:11]1[CH2:12][CH2:13][C:8]([CH3:20])([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:24]([CH2:21][CH2:22][CH3:23])(=[O:26])=[O:25])[CH:3]=2)[CH2:9][CH2:10]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 662791-Propanesulfonyl chlorideHCID 23000931HCID 23000931, compound

Product 2

HCID 222AmmoniaHCID 54458887HCID 54458887, compoundYield 161.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 4-(3-aminophenyl)-N-hexyl-4-methylpiperidine (Preparation 56, 72.0 mg, 0.26 mmol) in dichloromethane (1 ml) was added n-propanesulfonyl chloride (75 mg, 0.53 mmol) in dichloromethane (1 ml) and pyridine (42 mg, 0.53 mmol) in dichloromethane (1 ml) at room temperature. The solution was stirred at room temperature for 20 h, then it was concentrated in vacuo to give the crude product. This was purified by silica column chromatography eluting with ethyl acetate:0.880 ammonia (100:1) to give the title compound as a colourless oil (80 mg, 80%).

Workup

  1. concentrationit was concentrated in vacuo
  2. customto give the crude product
  3. customThis was purified by silica column chromatography
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-615366c7a5d54795a182a7d3336625ae
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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