Water → 1-Acetyl-N-{3-[4-(4-aminoanilino)-1-piperidinyl]propyl}-N-(3,4-dichlorophenyl)-4-piperidinecarboxamide

HRID 412943

反応式

HRID 412943 の反応式
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([N:12]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=2)[CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+].C(OCC)(=O)C.O>C(OC(C)C)(C)C.CCCCCC.[Ni](Br)Br>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]([N:12]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=3)[CH2:20][CH2:21]2)[C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=2)=[O:11])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 185390691-Acetyl-N-(3,4-dichlorophenyl)-N-{3-[4-(4-nitroanilino)-1-piperidinyl]propyl}-4-piperidinecarboxamide

生成物 1

HCID 185388641-Acetyl-N-{3-[4-(4-aminoanilino)-1-piperidinyl]propyl}-N-(3,4-dichlorophenyl)-4-piperidinecarboxamide収率 65.4%

試薬・触媒・溶媒 2

HCID 278492Nickel(II) bromide触媒HCID 21881879Diisopropylether hexane溶媒

実験手順

To a solution of the compound obtained in Example 219 (162 mg, 0.26 mmol) in methanol/THF (1/1, 10 mL) were added nickel bromide (II)(5.7 mg) and sodium borohydride (40 mg, 1.1 mmol), and the mixture was stirred at room temperature for 10 minutes. To the reaction mixture were added ethyl acetate (20 mL) and water (20 mL), and the insolubles were filtered off with Celite. The organic layer was washed with saturated aqueous solution of sodium chloride (10 ml), dried with anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to flash column chromatography (alumina 2 g, ethyl acetate/methanol=1/0 to 10/1), and the desired fraction was concentrated under reduced pressure to give the titled compound (99 mg, 0.17 mmol, Yield 64%) as pale yellow amorphous substance.

後処理

  1. filtrationthe insolubles were filtered off with Celite
  2. washThe organic layer was washed with saturated aqueous solution of sodium chloride (10 ml)
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. concentrationthe desired fraction was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-0cc3015dd9da46a6bd9631c66d71c1b9
出典データセット
uspto-grants-2003_05
特許番号
US06562978B1

関連ノート

読み込み中…