1,2-Dichloroethane → 1-[(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)acetyl]-4-(2,3,4-trimethoxybenzyl)piperazine

HRID 568735

反応式

HRID 568735 の反応式
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.N1C=CC=CC=1.ClCCCl.[CH3:30][O:31][C:32]1[C:33]([CH3:49])=[C:34]([CH3:48])[C:35]2[O:40][C:39]([CH2:42][C:43](Cl)=[O:44])([CH3:41])[CH2:38][CH2:37][C:36]=2[C:46]=1[CH3:47]>O>[CH3:30][O:31][C:32]1[C:33]([CH3:49])=[C:34]([CH3:48])[C:35]2[O:40][C:39]([CH2:42][C:43]([N:17]3[CH2:16][CH2:15][N:14]([CH2:13][C:4]4[CH:5]=[CH:6][C:7]([O:11][CH3:12])=[C:8]([O:9][CH3:10])[C:3]=4[O:2][CH3:1])[CH2:19][CH2:18]3)=[O:44])([CH3:41])[CH2:38][CH2:37][C:36]=2[C:46]=1[CH3:47]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 1049PyridineHCID 21109TrimetazidineHCID 20150413(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)acetyl chloride

生成物 1

HCID 201503791-[(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)acetyl]-4-(2,3,4-trimethoxybenzyl)piperazine収率 26.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution composed of 2.54 g (0.01 mol) of 1-(2,3,4-trimethoxyphenyl)methylpiperazine, 0.95 g of pyridine and 50 ml of 1,2-dichloroethane was added 3.56 g (0.012 mol) of the (3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)acetyl chloride prepared above and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water and extracted with diethyl ether. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and filtered. Low-boiling substances were distilled off from the filtrate under reduced pressure and the residue was purified by silica gel column chromatography. The eluate was further purified by recrystallization from a 95:5 (v/v) mixture of hexane and ethyl acetate to give 1.4 g of 1-[(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)acetyl]-4-(2,3,4-trimethoxybenzyl)piperazine [Compound (28)] having the following physical characteristics.

後処理

  1. customprepared above and the mixture
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationLow-boiling substances were distilled off from the filtrate under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. customThe eluate was further purified by recrystallization from a 95:5 (v/v) mixture of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-49fc9e2515cc4b79a3c51084ac97574c
出典データセット
uspto-grants-1988_03
特許番号
US04728650

関連ノート

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