4-[2-(3,4-Dichlorophenyl)-[1,3]dioxolan-2-yl]piperidine → N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamide

HRID 369930노트

반응식

HRID 369930 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[O:13][CH2:12][CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:20]1([CH3:35])[CH:25]=[CH:24][C:23]([C:26]([NH:28][C@H:29]([CH:33]=O)[CH:30]([CH3:32])[CH3:31])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:14]3[CH2:19][CH2:18][N:17]([CH2:33][CH:29]([NH:28][C:26](=[O:27])[C:23]4[CH:22]=[CH:21][C:20]([CH3:35])=[CH:25][CH:24]=4)[CH:30]([CH3:31])[CH3:32])[CH2:16][CH2:15]3)[O:13][CH2:12][CH2:11][O:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

4

반응물 2

HCID 232831594-[2-(3,4-Dichlorophenyl)-[1,3]dioxolan-2-yl]piperidineHCID 53763109N-p-toluoyl valinaldehyde

생성물 1

HCID 23283153N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamide수율 52.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 4-[2-(3,4-dichlorophenyl)-[1,3]dioxolan-2-yl]piperidine (0.21 g, 0.7 mmol), N-p-toluoyl valinaldehyde (0. 17g, 0.764 mmol), sodium triactetoxy-borohydride (0.22 g, 1.04 mmol) in methylene chloride (20 mL) was stirred overnight under argon. After concentrating the reaction mixture, the residue was stirred with ethyl acetate and dilute aqueous potassium carbonate solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The crude was flash chromatographed on flash silica gel with 1% methanol/methylene chloride (containing 1% ammonia) to give N-(1-{4-[2-(3,4-dichlorophenyl)-[1,3 ]dioxolan-2-yl]piperidin-1-yl-methyl}-2-methylpropyl)-4-methylbenzamide (0.187g, 0.366 mmoles).

후처리

  1. concentrationAfter concentrating the reaction mixture
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customchromatographed on flash silica gel with 1% methanol/methylene chloride (containing 1% ammonia)

출처 및 근거

ORD 기록
ord-d2c08ea8c2c440ecb770271c253a9353
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140344

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