Homoveratrylamine → 7,7-Dimethyl-2-phenethyl-5-[2-(2-(3,4-dimethoxy-phenyl)ethylamino)-ethyl]-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione dihydrochloride

HRID 47117Notes

Reaction equation

HRID 47117 reaction equation
[CH3:1][C:2]1([CH3:28])[C:11](=[O:12])[CH:10]2[C:5](=[C:6]3[N:19]=[C:18]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:17]=[C:7]3[C:8](=[O:16])[CH:9]2[CH2:13][CH2:14][Cl:15])[CH:4]=[N:3]1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH2:39][CH2:40][NH2:41])[CH:34]=[CH:35][C:36]=1[O:37][CH3:38]>CCOCC>[ClH:15].[ClH:15].[CH3:1][C:2]1([CH3:28])[C:11](=[O:12])[CH:10]2[C:5](=[C:6]3[N:19]=[C:18]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:17]=[C:7]3[C:8](=[O:16])[CH:9]2[CH2:13][CH2:14][NH:41][CH2:40][CH2:39][C:33]2[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:31]([O:30][CH3:29])[CH:32]=2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 8421HomoveratrylamineHCID 706106487,7-Dimethyl-2-phenethyl-5-(2-chloro-ethyl)-5H,7H-imidazo-[4,5-h]isoquinoline-4,6-dione

Product 1

HCID 706110287,7-Dimethyl-2-phenethyl-5-[2-(2-(3,4-dimethoxy-phenyl)ethylamino)-ethyl]-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione dihydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.8 gm of 7,7-dimethyl-2-phenethyl-5-(2-chloro-ethyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione were heated at 150° C. for 40 minutes with 5 ml of 2-(3,4-dimethoxy-phenyl)-ethylamine. After cooling, the mixture was dissolved in ether, and the solution was several times extracted with water weakly acidified with acetic acid. The organic phase was evaporated, and the residue was dissolved in acetone. The dihycrochloride was precipitated from the acetone solution with ethereal hydrochloric acid.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with water
  3. customThe organic phase was evaporated
  4. dissolutionthe residue was dissolved in acetone
  5. customThe dihycrochloride was precipitated from the acetone solution with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-7c3769ac7cc947aca77924770f7da1d2
Source dataset
uspto-grants-1979_11
Patent number
US04176184

Reaction notes

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