N-Benzylnormechlorethamine → N-benzylpiperidine-1-sulfonamide

반응식

[CH2:1]=[N:2][SH:3](=[O:5])=[O:4].[C:6](=O)([O-])[O-].[K+].[K+].ClCCN(CCCl)C[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1O[CH2:42][CH2:41]OCCOCCOCCOCCOC1.[CH3:44][N:45]([CH3:48])C=O>>[CH2:1]([NH:2][S:3]([N:45]1[CH2:48][CH2:42][CH2:41][CH2:6][CH2:44]1)(=[O:5])=[O:4])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

반응물 5

HCID 5928N-Benzylnormechlorethamine

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 2855718-Crown-6

HCID 178486263HCID 178486263, 화합물

생성물 1

HCID 2989594N-benzylpiperidine-1-sulfonamide수율 52%

실험 절차

To a solution of the methylene sulfonamide from part F (20.46 g, 51.5 mmol) in dimethylformamide (90 mL) was added potassium carbonate (21.3 g, 154.7 mmol), bis-(2-chloroethyl)benzyl amine (12.0 g, 51.5 mmol; and 18-Crown-6 (700 mg). The slurry was stirred at sixty degrees Celsius. After twenty four hours the reaction was concentrated in vacuo. The residue was taken up in ethyl acetate, washed with water three times, saturated sodium chloride solution, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was recrystallized (methanol) to give the N-benzyl piperidine sulfonamide as a white solid (15 g, 52%).