N-Acetylsulfanilyl chloride → N-{4-[(1-Butylpiperidin-4-yl)sulfamoyl]phenyl}acetamide

HRID 1580686Notes

Reaction equation

HRID 1580686 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9](Cl)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:17]1.C(=O)(O)[O-].[Na+]>O.C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([S:9]([NH:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:17]2)(=[O:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 8481N-Acetylsulfanilyl chlorideHCID 516892Sodium BicarbonateHCID 122628201-Butylpiperidin-4-amine

Product 1

HCID 21563541N-{4-[(1-Butylpiperidin-4-yl)sulfamoyl]phenyl}acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

7.0 Grams of N-acetylsulphanilyl chloride were added in portions to a stirred, ice cooled, mixture of 4.7 grams of 4-amino-1-n-butyl piperidine and 6.3 grams of sodium bicarbonate in 75 milliliters of water and 35 milliliters of chloroform. After stirring overnight at room temperature the mixture was filtered, washed with water, and dried to give 4.2 grams of the title compound. Melting Point 174°-175°C.

Workup

  1. temperaturecooled
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-9affc9fbd6fb42b2a10829af12de4f92
Source dataset
uspto-grants-1976_01
Patent number
US03933829

Reaction notes

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