Triethylamine → HCID 21510411, compound

HRID 1577009Notes

Reaction equation

HRID 1577009 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][CH:6]3[CH2:11][CH2:12][NH:13][CH2:14][CH:5]3[C:4]=2[CH:3]=1.Br[CH2:16][CH2:17][CH2:18][C:19]#[N:20].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:19]([CH2:18][CH2:17][CH2:16][N:13]1[CH2:12][CH2:11][CH:6]2[NH:7][C:8]3[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=3[CH:5]2[CH2:14]1)#[N:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 214124-BromobutyronitrileHCID 10241582HCID 10241582, compound

Product 1

HCID 21510411HCID 21510411, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In toluene (60 ml) are dissolved 8-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (5.7 g), γ-bromobutyronitrile (4.5 g) and triethylamine (4.6 g), and the mixture is refluxed for 5 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 (5.5 g), m.p. 160° - 165°C (recrystallized from aqueous ethanol).

Workup

  1. temperaturethe mixture is refluxed for 5 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 (5.5 g), m.p. 160° - 165°C (recrystallized from aqueous ethanol)

Sources & evidence

ORD record
ord-c9525070d3584fa8bfc2efa750d26c21
Source dataset
uspto-grants-1976_09
Patent number
US03983239

Reaction notes

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