4-Piperidino-6-quinazolinesulfonyl chloride → N-(4-aminobutyl)-4-piperidino-6-quinazolinesulfonamide

HRID 1980570Notes

Reaction equation

HRID 1980570 reaction equation
[NH2:1][CH:2]=[CH:3][CH2:4][CH2:5][NH2:6].[N:7]1([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([S:23](Cl)(=[O:25])=[O:24])[CH:21]=3)[N:16]=[CH:15][N:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C(Cl)(Cl)Cl>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:23]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][N:14]=[C:13]2[N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 130442344-Piperidino-6-quinazolinesulfonyl chlorideHCID 734475401,4-Diaminobutene

Product 1

HCID 13044235N-(4-aminobutyl)-4-piperidino-6-quinazolinesulfonamideYield 77.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

In 100 ml of chloroform was dissolved 4.4 g of 1,4-diaminobutene, and to the solution was added dropwise 50 ml of a chloroform solution containing 3.1 g of 4-piperidino-6-quinazolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution was stirred at a temperature of 20° C. to 25° C. for two hours, and the reaction solution was extracted with a 10% aqueous hydrochloric acid solution. The chloroform layer was washed with water and dried with anhydrous potassium carbonate. Then chloroform was distilled from the chloroform layer, and the residue was separated by Prep LC/System 500 (Waters Associates, U.S.A.) [column: Prepack 500/C18 ; solvent: H2O/CH3CN=85/15 (volume ratio); flow rate: 100 ml/minute] to give 2.8 g of N-(4-aminobutyl)-4-piperidino-6-quinazolinesulfonamide [i.e. Compound(31)] as an oily substance in a yield of 77%.

Workup

  1. temperatureunder cooling with ice
  2. extractionthe reaction solution was extracted with a 10% aqueous hydrochloric acid solution
  3. washThe chloroform layer was washed with water
  4. dry with materialdried with anhydrous potassium carbonate
  5. distillationThen chloroform was distilled from the chloroform layer
  6. customthe residue was separated by Prep LC/System 500 (Waters Associates, U.S.A.) [column: Prepack 500/C18 ; solvent: H2O/CH3CN=85/15 (volume ratio); flow rate: 100 ml/minute]

Sources & evidence

ORD record
ord-44eadc7e5f8c4e93b68d3b9da50cc8ae
Source dataset
uspto-grants-1985_04
Patent number
US04510307

Reaction notes

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