Pyridine → HCID 23000955, compound

HRID 397708Notes

Reaction equation

HRID 397708 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:23](Cl)(=[O:25])=[O:24])[CH3:22].N1C=CC=CC=1>ClCCl>[NH3:1].[CH2:21]([S:23]([NH: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)(=[O:25])=[O:24])[CH3:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 23000931HCID 23000931, compound

Product 2

HCID 222AmmoniaHCID 23000955HCID 23000955, compoundYield 166.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 4-(3-aminophenyl)-N-hexyl-4-methylpiperidine (Preparation 56, 50.0 mg, 0.18 mmol) in dichloromethane (1 ml) was added ethanesulfonyl chloride (47 mg, 0.37 mmol) in dichloromethane (1 ml) and pyridine (30 mg, 0.37 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:hexane:0.880 ammonia (98:2:1) to give the title compound as a colourless oil (55 mg, 82%).

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-540c71138d534339bc62465338428525
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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