1,2-Dichloroethane → HCID 67130576、化合物

HRID 2380961ノート

反応式

HRID 2380961 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.Cl[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[Cl:49]CCCl>>[Cl:49][C:30]1[CH:29]=[CH:28][C:25]([CH2:26][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]([N:10]3[CH2:15][CH2:14][N:13]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:12][CH2:11]3)=[O:9])=[CH:6][CH:7]=2)=[CH:24][CH:23]=1

参加物

6

反応物 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 114773-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 12932882(4-Aminophenyl)(4-phenylpiperazin-1-yl)methanone

生成物 1

HCID 67130576HCID 67130576、化合物収率 25%

実験手順

To a stirred solution of (4-amino-phenyl)-(4-phenyl-piperazin-1-yl)-methanone (200 mg, 0.71 mmol) in 1,2-dichloroethane (4 ml) at 0° C. was added 3-chlorobenzaldehyde (99.7 mg, 0.71 mmol). Sodium triacetoxy borohydride (210 mg, 0.99 mmol) and acetic acid (40.6 μl, 0.71 mmol) were added and the reaction was stirred at room temperature under nitrogen overnight. The reaction was quenched with the addition of sodium hydroxide (aq.) (pH8) and extracted with diethyl ether (3×20 ml). The organic extracts were combined, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound as a yellow solid (72 mg, 25% yield). HPLC retention time 7.5 min. Mass spectrum (ES+) m/z 406 (M+H).

後処理

  1. customThe reaction was quenched with the addition of sodium hydroxide (aq.) (pH8)
  2. extractionextracted with diethyl ether (3×20 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-179fa51d375149e885fef553c0829395
出典データセット
uspto-grants-2012_09
特許番号
US08258138B2

反応ノート

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