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 369930ノート

反応式

HRID 369930 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d2c08ea8c2c440ecb770271c253a9353
出典データセット
uspto-grants-2000_10
特許番号
US06140344

反応ノート

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