1,2,3,4-Tetrahydroisoquinoline → Benzamide, 3,4-dimethoxy-N-(1,2,3,4-tetrahydro-2-propylisoquinolin-5-yl)-
Reaction equation
Br.[NH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH2:13][CH2:14][CH3:15])[CH2:8]2.C(=O)(O)[O-].[K+].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[C:26](Cl)=[O:27].C1C2C(=CC=CC=2)CCN1>C1C=CC=CC=1>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[C:26]([NH:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH2:13][CH2:14][CH3:15])[CH2:8]2)=[O:27]Participants
Procedure
5-Amino-2-n-propyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (10 g) prepared as in Example 5 was suspended in dry benzene (100 ml) and 0.5 g dry potassium bicarbonate was added. A 0.1 mole excess of 3,4-dimethoxybenzoyl chloride was dissolved in dry benzene (100 ml) and this solution was added to the solution of the tetrahydroisoquinoline. The mixture was refluxed for 5 days. The precipitate formed at the end of this period was collected by filtration and washed with 10% sodium carbonate solution followed by water. The washings were discarded and the remaining solid was purified by recrystallization from ethanol to yield 6.7 g of 5-(3,4-dimethoxybenzamido)-2-n-propyl-1,2,3,4-tetrahydroisoquinoline as a white powder, m.p. 146°-147° C.
Workup
- temperatureThe mixture was refluxed for 5 days
- customThe precipitate formed at the end of this period
- filtrationwas collected by filtration
- washwashed with 10% sodium carbonate solution
- customthe remaining solid was purified by recrystallization from ethanol
Sources & evidence
- ORD record
- ord-caa5ce1749474bb4813e7c504d20b82b
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04022900
Reaction notes
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