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

HRID 1831831Notes

Reaction equation

HRID 1831831 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-0cbda807d5cd4009a5e8864e20c7f861
Source dataset
uspto-grants-2006_06
Patent number
US07067670B2

Reaction notes

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