Toluene → HCID 12527896, compound

HRID 1577008Notes

Reaction equation

HRID 1577008 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]1[CH:17]=[CH:16][C:15]2[NH:14][CH:13]3[CH2:18][CH2:19][NH:20][CH2:21][CH:12]3[C:11]=2[CH:10]=1.C(Cl)C1C=CC=CC=1>C(N(CC)CC)C>[CH2:7]([N:20]1[CH2:19][CH2:18][CH:13]2[NH:14][C:15]3[CH:16]=[CH:17][C:9]([CH3:8])=[CH:10][C:11]=3[CH:12]2[CH2:21]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7503Benzyl ChlorideHCID 10241582HCID 10241582, compound

Product 1

HCID 12527896HCID 12527896, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To toluene (100 ml) are added 8-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (10 g), benzyl chloride (7.4 g) and triethylamine (8.1 g), and the mixture is refluxed for 15 hours. After cooling, the reaction mixture is washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove toluene. The resulting residue is treated with ethanolic hydrogen chloride in the same manner as described in Example 1 (1) to give the dihydrochloride of the titled compound (11.0 g), m.p. 179° - 182°C (recrystallized from ethanol).

Workup

  1. temperaturethe mixture is refluxed for 15 hours
  2. temperatureAfter cooling
  3. washthe reaction mixture is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove toluene
  7. additionThe resulting residue is treated with ethanolic hydrogen chloride in the same manner
  8. customto give
  9. customthe dihydrochloride of the titled compound (11.0 g), m.p. 179° - 182°C (recrystallized from ethanol)

Sources & evidence

ORD record
ord-6de45e9e95ad4ccaa14bb38de3962931
Source dataset
uspto-grants-1976_09
Patent number
US03983239

Reaction notes

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