1,2,3,4-Tetrahydroisoquinoline → Benzamide, N-(1,2,3,4-tetrahydro-2-methylisoquinolin-7-yl)-3,4,5-trimethoxy-

HRID 2397936Notes

Reaction equation

HRID 2397936 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH3:12])[CH2:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[N+](C1C=C2C(C=C[N+](C)=C2)=CC=1)([O-])=O.C(=O)(O)[O-].[K+].[CH3:43][O:44][C:45]1[CH:46]=[C:47]([CH:51]=[C:52]([O:56][CH3:57])[C:53]=1[O:54][CH3:55])[C:48](Cl)=[O:49].C1C2C(=CC=CC=2)CCN1>C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:57][O:56][C:52]1[CH:51]=[C:47]([CH:46]=[C:45]([O:44][CH3:43])[C:53]=1[O:54][CH3:55])[C:48]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH3:12])[CH2:9]2)=[CH:4][CH:3]=1)=[O:49]

Participants

8

Reactant 5

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516893Potassium BicarbonateHCID 129995062-Methyl-1,2,3,4-tetrahydroisoquinolin-7-amineHCID 21436756HCID 21436756, compound

Product 1

HCID 216591Benzamide, N-(1,2,3,4-tetrahydro-2-methylisoquinolin-7-yl)-3,4,5-trimethoxy-

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

7-Amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (2 g), prepared from 7-nitro-2-methyl-isoquinolinium p-toluenesulfonate as described for the 5-nitro isomer in Example 4 was dissolved in dry benzene (50 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 benzene (50 ml) and this solution was added to the solution of the tetrahydroisoquinoline. A brown precipitate formed immediately and the mixture was refluxed for 3 hours. The benzene was removed in vacuo leaving a tan residue which was suspended in 10% sodium carbonate solution to remove excess acid chloride and stirred for 1 hour. The insoluble residue was a brown oil which was extracted from the aqueous sodium carbonate with chloroform. The chloroform was dried over anhydrous magnesium sulfate and the chloroform was distilled off to leave a viscous red oil which crystallized to a white powder (2.7 g) when washed with cold ether. The white solid was recrystallized from ethanol-ether to yield the desired product as a white powder, m.p. 157.5°-158° C.

Workup

  1. customA brown precipitate formed immediately
  2. temperaturethe mixture was refluxed for 3 hours
  3. customThe benzene was removed in vacuo
  4. customleaving a tan residue which
  5. customto remove excess acid chloride
  6. extractionwas extracted from the aqueous sodium carbonate with chloroform
  7. dry with materialThe chloroform was dried over anhydrous magnesium sulfate
  8. distillationthe chloroform was distilled off
  9. customto leave a viscous red oil which
  10. customcrystallized to a white powder (2.7 g) when
  11. washwashed with cold ether
  12. customThe white solid was recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-7a8c5ea54e784e42bda22c23f477b0d8
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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