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N-Benzylnormechlorethamine → N-benzylpiperidine-1-sulfonamide

HRID 842241
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HRID 842241 반응식
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
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7

반응물 5

HCID 5928N-BenzylnormechlorethamineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 22052576HCID 22052576, 화합물HCID 178486263HCID 178486263, 화합물

생성물 1

HCID 2989594N-benzylpiperidine-1-sulfonamide수율 52%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c13dcb6d5c41400d933a010f8c6545d2
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06372758B1

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