HCID 17794322, compound → HCID 22503495, compound

HRID 1814451Notes

Reaction equation

HRID 1814451 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Sn](CCCC)(CCCC)CCCC)=[CH:10][C:9]=1[O:27][CH3:28])(=[O:3])[CH3:2].[CH2:29]([N:31]1[CH2:36][CH2:35][N:34]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39][N:38]=2)[CH2:33][CH2:32]1)[CH3:30]>C1(C)C(C)=CC=CC=1>[CH2:29]([N:31]1[CH2:32][CH2:33][N:34]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[C:39]([C:11]3[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])=[C:9]([O:27][CH3:28])[CH:10]=3)[N:38]=2)[CH2:35][CH2:36]1)[CH3:30]

Participants

4

Reactant 2

HCID 17794322HCID 17794322, compoundHCID 22502645HCID 22502645, compound

Product 1

HCID 22503495HCID 22503495, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-(3-Acetoxypropyl)-5-tributylstannylanisole (0.92 g) and 3-bromo-1-((4-ethylpiperazin-1-yl)isoquinoline (0.37 g) were reacted in the presence of tetrakistriphenylphosphine (0.3 g) in xylene in nitrogen atmosphere for 4 hr. After cooling, the reaction solution was filtered and extracted with ethyl acetate. The resulting organic layer was washed with water and brine, dried and concentrated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 0.28 g of the title compound. (33-2) 1-(4-Ethylpiperazin-1-yl)-3-[4-(3-hydroxypropyl)-3-methoxyphenyl]isoquinoline hydrochloride

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction solution was filtered
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic layer was washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-d5c8e2b1b02f41cbb7b786363aa0f28e
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

Loading…