Triethylamine → 3-Methyl 1-(4-nitrophenyl) 5-[4-(trifluoromethyl)phenyl]piperidine-1,3-dicarboxylate

HRID 2091744ノート

反応式

HRID 2091744 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:39])[O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1>ClCCl>[F:20][C:2]([F:19])([F:1])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:28]([O:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)=[O:39])[CH2:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58002265Methyl 5-(4-(trifluoromethyl)phenyl)piperidine-3-carboxylate

生成物 1

HCID 580023253-Methyl 1-(4-nitrophenyl) 5-[4-(trifluoromethyl)phenyl]piperidine-1,3-dicarboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

20.0 g (69.6 mmol) of methyl 5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxylate (Example 13A) were dissolved in 1.0 l of dichloromethane, and admixed at 0° C. with 14.1 g (139 mmol) of triethylamine Subsequently, 14.0 g (69.6 mmol) of 4-nitrophenyl chlorocarbonate were added dropwise. The reaction mixture was stirred at 0° C. for 2 h and then at RT for 16 h. For workup, the mixture was washed with saturated aqueous sodium hydrogencarbonate solution. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. This gave 31.3 g of crude product, which was reacted without any further purification steps.

後処理

  1. waitat RT for 16 h
  2. washFor workup, the mixture was washed with saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThis gave 31.3 g of crude product, which was reacted without any further purification steps

出典と根拠

ORDレコード
ord-df2483d00bfc43e08c14826da530e556
出典データセット
uspto-grants-2013_05
特許番号
US08440657B2

反応ノート

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