Homoveratrylamine → HCID 12751786, compound

HRID 1577936Notes

Reaction equation

HRID 1577936 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][CH2:17][CH:18]([OH:21])[CH2:19][Cl:20])=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11][CH2:10]2)[C:2]#[CH:3].C(=O)([O-])[O-].[K+].[K+].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH2:38][CH2:39][NH2:40])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]>CO>[ClH:20].[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([O:16][CH2:17][CH:18]([OH:21])[CH2:19][NH:40][CH2:39][CH2:38][C:32]2[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:30]([O:29][CH3:28])[CH:31]=2)=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH2:11][CH2:10]2)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 8421HomoveratrylamineHCID 11430Potassium CarbonateHCID 20570384HCID 20570384, compound

Product 1

HCID 12751786HCID 12751786, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.0 g of 8-(2-propynyloxy)-5-(3-chloro-2-hydroxypropoxy)-3,4-dihydrocarbostyril was dissolved in 20 ml of methanol. 0.5 g of anhydrous potassium carbonate and 1.6 g of 2-(3,4-dimethoxyphenyl)ethylamine were added thereto, and the resulting mixture was stirred while refluxing for 2.5 hours. After completion of the reaction, the methanol was evaporated under reduced pressure, and the residue was dissolved in chloroform and then washed with water. The chloroform layer was dried over anhydrous sodium sulfate, and the chloroform evaporated under reduced pressure. The residue was recrystallized from methanol-diethyl ether to obtain 1.1 g of 8-(2-propynyloxy)-5-{3-[2-(3,4-dimethoxyphenyl)ethylamino]-2-hydroxypropoxy}-3,4-dihydrocarbostyril hydrochloride having a melting point of 160°-162° C.

Workup

  1. temperaturewhile refluxing for 2.5 hours
  2. customAfter completion of the reaction
  3. customthe methanol was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with water
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  7. customthe chloroform evaporated under reduced pressure
  8. customThe residue was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-5813944496f045d6aa66af743e91ed6f
Source dataset
uspto-grants-1981_09
Patent number
US04289883

Reaction notes

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