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N-Benzylnormechlorethamine → N-benzylpiperidine-1-sulfonamide

HRID 842241
Notes
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Reaction equation

HRID 842241 reaction equation
C1(CN2CCC([S:18]([N:21]3[CH2:26][CH2:25][CH:24](OC4C=CC(OC(F)(F)F)=CC=4)[CH2:23][CH2:22]3)(=[O:20])=[O:19])(C(OC)=O)CC2)C=CC=CC=1.C=NS(=O)=O.C(=O)([O-])[O-].[K+].[K+].ClCC[N:53](CCCl)[CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[CH2:54]([NH:53][S:18]([N:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)(=[O:19])=[O:20])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 5928N-BenzylnormechlorethamineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 22052576HCID 22052576, compoundHCID 178486263HCID 178486263, compound

Product 1

HCID 2989594N-benzylpiperidine-1-sulfonamideYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Part G: Preparation of methyl 1-(phenylmethyl)-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]sulfonyl]-4-piperidinecarboxylate. 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 60° C. After twenty four hr 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 hr 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-c13dcb6d5c41400d933a010f8c6545d2
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06372758B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes