Water → 4-[(1-Acetylpiperidin-4-yl)methyl]benzene-1-sulfonyl chloride

HRID 1006377Notes

Reaction equation

HRID 1006377 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)(=[O:8])[CH3:7].O>ClCCl>[C:6]([N:9]1[CH2:10][CH2:11][CH:12]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:20][CH:21]=2)[CH2:13][CH2:14]1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 299608N-Acetyl-4-benzylpiperidine

Product 1

HCID 226766334-[(1-Acetylpiperidin-4-yl)methyl]benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To chlorosulfonic acid (92 mL), a solution of 1-acetyl-4-benzylpiperidine (60.00 g) in dichloromethane (100 mL) was dropwise added for an hour at 0° C. under stirring, and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 1.5 hours. The reaction mixture was poured into ice-cooled water (1 L) and extracted with dichloromethane (500 mL, 250 mL). The organic phase was washed with an aqueous solution of 5% sodium carbonate (500 mL×2) and saturated brine (250 mL). The organic phase was dried over magnesium sulfate (anhydrous), and concentrated under reduced pressure. The residue was subjected to column chromatography (silica gel 250 g, ethyl acetate). The objective fraction was concentrated under reduced pressure to give the title compound as a white solid (54.22 g).

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 minutes and at room temperature for 1.5 hours
  2. additionThe reaction mixture was poured into ice-
  3. extractionextracted with dichloromethane (500 mL, 250 mL)
  4. washThe organic phase was washed with an aqueous solution of 5% sodium carbonate (500 mL×2) and saturated brine (250 mL)
  5. dry with materialThe organic phase was dried over magnesium sulfate (anhydrous)
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe objective fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9c165859e2ac46ec8da89fa1edb05c0f
Source dataset
uspto-grants-2004_09
Patent number
US06787650B1

Reaction notes

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