N-Benzylnormechlorethamine → N-(Phenylmethyl)-1-piperidinesulfonamide

HRID 2297584Notes

Reaction equation

HRID 2297584 reaction equation
[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

Participants

6

Reactant 5

HCID 5928N-BenzylnormechlorethamineHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 178486263HCID 178486263, compound

Product 1

HCID 2989594N-(Phenylmethyl)-1-piperidinesulfonamideYield 52%

Procedure

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%).

Workup

  1. concentrationAfter twenty four hours the reaction was concentrated in vacuo
  2. washwashed with water three times, saturated sodium chloride solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized (methanol)

Sources & evidence

ORD record
ord-ba6e541de60a46eca31d75f5d15427c0
Source dataset
uspto-grants-2002_12
Patent number
US06492367B1

Reaction notes

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