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

Reaction equation

HRID 568735 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-49fc9e2515cc4b79a3c51084ac97574c
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Linked notes

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