Chlorosulfonic acid → 4-(1-Acetylpiperidin-4-yl)benzenesulphonyl chloride

HRID 1762837Notes

Reaction equation

HRID 1762837 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:16][S:17](O)(=[O:19])=[O:18]>>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([S:17]([Cl:16])(=[O:19])=[O:18])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 11608128HCID 11608128, compound

Product 1

HCID 200398204-(1-Acetylpiperidin-4-yl)benzenesulphonyl chloride

Procedure

1-Acetyl-4-phenylpiperidine, [Chem. Abs., 75, 5728b (1971] (16.30 g) was added portionwise over 1 hour to stirred chlorosulphonic acid (53.3 ml) at 0°. The solution was stirred at 0° for 1 hour, then at room temperature for 2 hours, and then finally poured cautiously onto an excess of ice. When the ice had melted the mixture was extracted several times with dichloromethane. The combined organic extracts were washed with water, dried (Na2SO4) and evaporated to give the title compound, (23.0 g), m.p. 133°-134°, used directly in the next step.

Workup

  1. waitat room temperature for 2 hours
  2. additionfinally poured cautiously onto an excess of ice
  3. extractionwas extracted several times with dichloromethane
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-7758a8711e374a31a578e2d63a02b74d
Source dataset
uspto-grants-1989_05
Patent number
US04835165

Reaction notes

Loading…