Sodium Carbonate → 4-(7-Chloro-4-quinolylamino)-N-(1-cyclohexyl-4-piperidyl)-benzene-sulphonamide

HRID 1580687Notes

Reaction equation

HRID 1580687 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.[NH2:24][CH:25]1[CH2:30][CH2:29][N:28]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:27][CH2:26]1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(Cl)(Cl)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]([NH:24][CH:25]4[CH2:30][CH2:29][N:28]([CH:31]5[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]5)[CH2:27][CH2:26]4)(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 47782391-Cyclohexylpiperidin-4-amineHCID 201495884-(7-Chloro-4-quinolinylamino)benzenesulphonyl chloride hydrochloride

Product 1

HCID 215635484-(7-Chloro-4-quinolylamino)-N-(1-cyclohexyl-4-piperidyl)-benzene-sulphonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

7.8 Grams of 4-(7-Chloro-4-quinolylamino)-benzenesulphonyl chloride hydrochloride [prepared as in Example 1(b)] were added in portions to a stirred ice-cooled mixture of 3.63 grams of 4-amino-1-cyclohexyl-piperidine and 21.2 grams of sodium carbonate in 60 milliliters of water and 50 milliliters of chloroform. After stirring overnight at room temperature the chloroform layer was separated, washed with water, dried and evaporated to give a brown solid. This was triturated with hexane, the resultant solid dissolved in chloroform and diiso-propyl ether added to precipitate a solid which was triturated with hexane to give 1.9 grams of the title compound as the hemihydrate. Melting point 192°-193°C.

Workup

  1. temperaturecooled
  2. customwas separated
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customto give a brown solid
  7. customThis was triturated with hexane
  8. dissolutionthe resultant solid dissolved in chloroform
  9. additiondiiso-propyl ether added
  10. customto precipitate a solid which
  11. customwas triturated with hexane

Sources & evidence

ORD record
ord-b92902003f104edbb495ca1b0bb62885
Source dataset
uspto-grants-1976_01
Patent number
US03933829

Reaction notes

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