1,2,3,4-Tetrahydroisoquinoline → Benzamide, N-(1,2,3,4-tetrahydro-2-propylisoquinolin-5-yl)-3,4,5-trimethoxy-

HRID 2397933Notes

Reaction equation

HRID 2397933 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]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[C:26](Cl)=[O:27].C1C2C(=CC=CC=2)CCN1>C1C=CC=CC=1>[CH3:35][O:34][C:30]1[CH:29]=[C:25]([CH:24]=[C:23]([O:22][CH3:21])[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

6

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516893Potassium BicarbonateHCID 21436740HCID 21436740, compound

Product 1

HCID 216588Benzamide, N-(1,2,3,4-tetrahydro-2-propylisoquinolin-5-yl)-3,4,5-trimethoxy-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5-Amino-2-n-propyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (13.7 g) prepared as in Example 5 was suspended in dry benzene (100 ml) and 0.5 g of dry potassium bicarbonate was added. A 0.1 mole excess of 3,4,5-trimethoxybenzoyl 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 was collected by filtration and washed with 10% sodium carbonate solution followed by water. The washings were discarded and the remaining solid (11.7 g) was purified by recrystallization from ethanol to yield 5-(3,4,5-trimethoxybenzamido)-2-n-propyl-1,2,3,4-tetrahydroisoquinoline as a white powder, m.p., 158.5°-159.5° C.

Workup

  1. temperatureThe mixture was refluxed for 5 days
  2. customThe precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed with 10% sodium carbonate solution
  5. customthe remaining solid (11.7 g) was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-7b8f29755dc6435eb0b9f9595988a9ca
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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