1,2-Dichloroethane → HCID 20150388, compound

HRID 568729Notes

Reaction equation

HRID 568729 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[CH3:16][O:17][C:18]1[CH:36]=[CH:35][C:21]2[CH2:22][CH2:23][C:24]([CH3:34])([CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[O:25][C:20]=2[CH:19]=1.N1C=CC=CC=1.ClCCCl>O>[CH3:16][O:17][C:18]1[CH:36]=[CH:35][C:21]2[CH2:22][CH2:23][C:24]([CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][N:31]([C:6](=[O:7])[C:5]4[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=4)[CH2:30][CH2:29]3)([CH3:34])[O:25][C:20]=2[CH:19]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 1049PyridineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 20150404HCID 20150404, compound

Product 1

HCID 20150388HCID 20150388, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,4,5-Trimethoxybenzoyl chloride (6.7 g, 0.029 mol) was added dropwise to a solution composed of 7.0 g (0.0241 mol) of 3,4-dihydro-7-methoxy-2-methyl-2-[2-(piperazin-1-yl)ethyl]-2H-benzopyran, 2.28 g of pyridine and 100 ml of 1,2-dichloroethane. The resultant mixture was stirred at room temperature for 2 hours. The reaction mixture obtained was poured into water and extracted with diethyl ether, the extract was dried over anhydrous sodium sulfate, and low-boiling substances were distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 5.0 g of 1-[2-(3,4-dihydro-7-methoxy-2-methyl-2H-benzopyran-2-yl)ethyl]-4-(3,4,5-trimethoxybenzoyl)piperazine [Compound (25)] having the following physical characteristics.

Workup

  1. customThe reaction mixture obtained
  2. extractionextracted with diethyl ether
  3. dry with materialthe extract was dried over anhydrous sodium sulfate, and low-boiling substances
  4. distillationwere distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-abbe7935dab646a1934a8440f3fdc913
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Reaction notes

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