Sodium Carbonate → 4-Dimethylamino-1-[4-(7-chloro-4-quinolylamino)-benzenesulphonyl]piperidine

HRID 1580684Notes

Reaction equation

HRID 1580684 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.Cl.Cl.[CH3:26][N:27]([CH3:34])[CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(Cl)(Cl)Cl>[CH3:26][N:27]([CH3:34])[CH:28]1[CH2:33][CH2:32][N:31]([S:20]([C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:7]3[C:6]4[C:11](=[CH:12][C:3]([Cl:2])=[CH:4][CH:5]=4)[N:10]=[CH:9][CH:8]=3)=[CH:15][CH:16]=2)(=[O:22])=[O:21])[CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201495884-(7-Chloro-4-quinolinylamino)benzenesulphonyl chloride hydrochlorideHCID 225914404-(Dimethylamino)piperidine dihydrochloride

Product 1

HCID 215635454-Dimethylamino-1-[4-(7-chloro-4-quinolylamino)-benzenesulphonyl]piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

11.3 Grams of 4-(7-chloro-4-quinolylamino)-benzenesulphonyl chloride hydrochloride [prepared as in Example 1(b)] were added in portions to a stirred mixture of 5.83 grams of 4-dimethylamino-piperidine dihydrochloride and 32 grams of sodium carbonate in 100 milliliters of water and 75 milliliters of chloroform. After stirring overnight at room temperature the mixture was filtered, the resultant solid washed with water, dried and recrystallised from ethanol/water to give 6.28 grams of the title compound. Melting point 230°--231°C.

Workup

  1. filtrationwas filtered
  2. washthe resultant solid washed with water
  3. customdried
  4. customrecrystallised from ethanol/water

Sources & evidence

ORD record
ord-be96c15de4da4d41b81fdc6f1aca3dbd
Source dataset
uspto-grants-1976_01
Patent number
US03933829

Reaction notes

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