3,4-Dimethoxyphenyl methyl ketone → 1-[4-Chloro-3-(trifluoromethyl)phenyl]-4-[1-(3,4-dimethoxyphenyl)ethyl]piperazine

HRID 1793437ノート

反応式

HRID 1793437 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:14]([F:17])([F:16])[F:15].[CH3:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)=O.[BH4-].[Na+]>CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=3)[CH3:18])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:14]([F:15])([F:17])[F:16]

参加物

6

反応物 3

HCID 143283,4-Dimethoxyphenyl methyl ketoneHCID 27781371-(4-Chloro-3-(trifluoromethyl)phenyl)piperazineHCID 4311764Sodium borohydride

生成物 1

HCID 101374521-[4-Chloro-3-(trifluoromethyl)phenyl]-4-[1-(3,4-dimethoxyphenyl)ethyl]piperazine

試薬・触媒・溶媒 2

HCID 178460666HCID 178460666、化合物触媒HCID 887Methanol溶媒

実験手順

A quantity of 0.17 g (0.6 mmole, 1 eq) of 1-(4-chloro-3-trifluoromethyl-phenyl)-piperazine and 0.1 g (0.6 mmole, 1 eq) of 3,4-dimethoxyacetophenone and 2 mL of Ti(OiPr)4 are warmed to 70° C. for 2 hours. The reaction solution is cooled to room temperature and 20 mL of anhydrous methanol is added followed by 1.0 g of NaBH4 and the resulting solution is stirred at room temperature for 2 hours. The reaction is quenched by the addition of 1 N NaOH and extracted with CH2Cl2. The CH2Cl2 extracts are dried over anhydrous MgSO4 and concentrated in vacuo. The residue is chromatographed on SiO2 with ethyl to afford 1-[4-chloro-3-(trifluoromethyl)phenyl]-4-[1-(3,4-dimethoxyphenyl)ethyl]piperazine (compound 2). Analysis 1H NMR (400 MHz, CDCl3): 7.31 (1H, d), 7.19 (1H, m), 6.90 (4H, m), 3.89 (6H, d), 3.38 (1H, m), 3.20 (4H, m), 2.61 (4H, m). MS (LC-MS): Calculated for C21H24ClF3N2O2 428.88, found 429.30 (M+).

後処理

  1. customThe reaction is quenched by the addition of 1 N NaOH
  2. extractionextracted with CH2Cl2
  3. dry with materialThe CH2Cl2 extracts are dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on SiO2 with ethyl

出典と根拠

ORDレコード
ord-c0a1f86b44244d6ba10f1cf103692e8a
出典データセット
uspto-grants-2006_07
特許番号
US07081458B2

反応ノート

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