Ethanol → (1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetic acid--1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxy-3,4-dihydroisoquinoline (1/1)

HRID 743032Notes

Reaction equation

HRID 743032 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][C:26]=1[O:27][CH2:28][CH3:29])[CH2:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:21][CH2:22][CH3:23])=[C:15]([O:18][CH2:19][CH3:20])[CH:16]=2)[CH2:11][CH2:10][NH+:9]=1)[CH3:2].[N:30]1([C:41](=[O:42])[C:40]2[N:39]([CH2:43][C:44]([O-:46])=[O:45])[CH:38]=[N:37][C:36]=2[N:34]([CH3:35])[C:32]1=[O:33])[CH3:31].[CH2:47]([O:49][C:50]1[CH:51]=[C:52]([CH:70]=[CH:71][C:72]=1[O:73][CH2:74][CH3:75])[CH2:53][C:54]1[C:63]2[C:58](=[CH:59][C:60]([O:67][CH2:68][CH3:69])=[C:61]([O:64][CH2:65][CH3:66])[CH:62]=2)[CH2:57][CH2:56][N:55]=1)[CH3:48].[N:76]1([C:87](=[O:88])[C:86]2[N:85]([CH2:89][C:90]([OH:92])=[O:91])[CH:84]=[N:83][C:82]=2[N:80]([CH3:81])[C:78]1=[O:79])[CH3:77].C(O)C>O.C(O)(C)C>[CH3:29][CH2:28][O:27][C:26]1[CH:25]=[CH:24][C:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:21][CH2:22][CH3:23])=[C:15]([O:18][CH2:19][CH3:20])[CH:16]=3)[CH2:11][CH2:10][N:9]=2)=[CH:5][C:4]=1[O:3][CH2:1][CH3:2].[CH3:35][N:34]1[C:32](=[O:33])[N:30]([CH3:31])[C:41](=[O:42])[C:40]2[N:39]([CH2:43][C:44]([OH:46])=[O:45])[CH:38]=[N:37][C:36]1=2.[OH2:49].[N:76]1([C:87](=[O:88])[C:86]2[N:85]([CH2:89][C:90]([O-:92])=[O:91])[CH:84]=[N:83][C:82]=2[N:80]([CH3:81])[C:78]1=[O:79])[CH3:77].[CH2:47]([O:49][C:50]1[CH:51]=[C:52]([CH:70]=[CH:71][C:72]=1[O:73][CH2:74][CH3:75])[CH2:53][C:54]1[C:63]2[C:58](=[CH:59][C:60]([O:67][CH2:68][CH3:69])=[C:61]([O:64][CH2:65][CH3:66])[CH:62]=2)[CH2:57][CH2:56][NH+:55]=1)[CH3:48]

Participants

8

Reactant 4

HCID 702EthanolHCID 13492HCID 13492, compound2×HCID 69550Acefylline2×HCID 70045402HCID 70045402, compound

Product 2

HCID 124905(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetic acid--1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxy-3,4-dihydroisoquinoline (1/1)HCID 19423821HCID 19423821, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

U.S. Pat. Nos. 4,814,336 and 4,820,838 disclose 1-(3',4'-diethoxybenzyl)-6,7-diethoxy-3,4-dihydroisoquinolinium-theophylline-7-acetate (Depogen). According to U.S. Pat. No. 4,820,838, Depogen is prepared by reacting equimolar amounts of 1-(3',4'-diethoxy-benzyl)-6,7-diethoxy-3,4-dihydro-isoquinoline with theophylline-7-acetic acid in an alcohol (preferably ethanol or isopropanol), cooling to precipitate a solid, and then filtering off the solid. In the process of U.S. Pat. No. 4,820,838 the crystalline monohydrate of 1-(3',4'-diethoxy-benzyl)-6,(7-diethoxy-3,4-dihydro-isoquinolinium-theophylline-7-acetate and if desired of pure 1-(3',4'-diethoxybenzyl)-6,7-diethoxy-3,4-dihydro-isoquinolinium-theophylline-7-acetate free of contaminating oxidation products is prepared by reacting 1-(3',4'-diethoxy-benzyl)-6,7-diethoxy-3,4-dihydro-isoquinoline with theophylline-7-acetic acid in the presence of water and one or more organic solvents, and if desired dehydrating the 1-(3',4'-diethoxy-benzyl)-6,7-diethoxy-3,4-dihydro-isoquinolinium-theophylline-7-acetate-monohydrate thus obtained. The organic solvent may be dichloromethane, a ketone such as acetone, or an alcohol such as isopropanol.

Workup

  1. temperaturecooling
  2. customto precipitate a solid
  3. filtrationfiltering off the solid
  4. customis prepared

Sources & evidence

ORD record
ord-63307d028cc640d0a3bf8e3b9d14329b
Source dataset
uspto-grants-1996_09
Patent number
US05556862

Reaction notes

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