Pyridine → HCID 23001032, compound

HRID 397707Notes

Reaction equation

HRID 397707 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.[CH3:21][S:22](Cl)(=[O:24])=[O:23].N1C=CC=CC=1>ClCCl>[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:22]([CH3:21])(=[O:24])=[O:23])[CH:3]=2)([CH3:20])[CH2:9][CH2:10]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 23000931HCID 23000931, compound

Product 2

HCID 222AmmoniaHCID 23001032HCID 23001032, compoundYield 136.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 4-(3-aminophenyl)-N-hexyl-4-methylpiperidine (Preparation 56, 70.0 mg, 0.27 mmol) in dichloromethane (3 ml) was added methanesulfonyl chloride (61 mg, 0.53 mmol) in dichloromethane (0.5 ml) and pyridine (42 mg, 0.53 mmol) in dichloromethane (0.5 ml) at room temperature. The solution was stirred at room temperature for 16 h, then it was concentrated in vacuo to give the crude product. This was purified by silica column chromatography eluting with a gradient of ethyl acetate:hexane:0.88 ammonia (90:10:1 to 98:2:1) to give the title compound as a colourless oil (65 mg, 72%).

Workup

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

Sources & evidence

ORD record
ord-561c5c0b599c4d02a44cc86961f14376
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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