1,2-Dichloroethane → 3,4-dihydro-6-methoxy-2-[2-[4-(3,4,5-trimethoxybenzoyl)piperazin-1-yl]ethyl]-2,5,7,8-tetramethyl-2H-benzopyran

HRID 568728Notes

Reaction equation

HRID 568728 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:24])=[C:5]([CH3:23])[C:6]2[O:11][C:10]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)([CH3:12])[CH2:9][CH2:8][C:7]=2[C:21]=1[CH3:22].ClCCCl.N1C=CC=CC=1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:43]=[C:44]([O:48][CH3:49])[C:45]=1[O:46][CH3:47])[C:40](Cl)=[O:41]>O>[CH3:1][O:2][C:3]1[C:4]([CH3:24])=[C:5]([CH3:23])[C:6]2[O:11][C:10]([CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][N:18]([C:40](=[O:41])[C:39]4[CH:38]=[C:37]([O:36][CH3:35])[C:45]([O:46][CH3:47])=[C:44]([O:48][CH3:49])[CH:43]=4)[CH2:19][CH2:20]3)([CH3:12])[CH2:9][CH2:8][C:7]=2[C:21]=1[CH3:22]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 1049PyridineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 139344873,4-dihydro-6-methoxy-2-[2-(piperazin-1-yl)ethyl]-2,5,7,8-tetramethyl-2H-benzopyran

Product 1

HCID 201503843,4-dihydro-6-methoxy-2-[2-[4-(3,4,5-trimethoxybenzoyl)piperazin-1-yl]ethyl]-2,5,7,8-tetramethyl-2H-benzopyranYield 62.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution composed of 2.0 g (6.02 mmol) of the 3,4-dihydro-6-methoxy-2-[2-(piperazin-1-yl)ethyl]-2,5,7,8-tetramethyl-2H-benzopyran obtained by the process of Example 12, 50 ml of 1,2-dichloroethane and 0.57 g of pyridine was ice-cooled in a nitrogen atmosphere and, to this solution, 1.67 g of 3,4,5-trimethoxybenzoyl chloride was added dropwise. The resultant mixture was stirred at room temperature overnight. The reaction mixture was then poured into water and extracted with diethyl ether. The ether layer was dried over anhydrous sodium sulfate. Low-boiling substances were distilled off under reduced pressure and the residue was purified by silica gel column chromatography to give 1.99 g of 3,4-dihydro-6-methoxy-2-[2-[4-(3,4,5-trimethoxybenzoyl)piperazin-1-yl]ethyl]-2,5,7,8-tetramethyl-2H-benzopyran [Compound (17)] having the following physical characteristics.

Workup

  1. additionwas added dropwise
  2. extractionextracted with diethyl ether
  3. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  4. distillationwere distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5b567a80570948c7b5863d94894c6dc9
Source dataset
uspto-grants-1988_03
Patent number
US04728650

Reaction notes

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