Acetic Acid → 2,3,4,9-tetrahydro-2-[2-(2-pyridinyl)ethyl]-1H-pyrido[3,4-b]indole

HRID 580647Notes

Reaction equation

HRID 580647 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)=[CH2:15].C(O)(=O)C>CO>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:14][CH2:15][N:2]1[CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:1]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 75212-VinylpyridineHCID 107838Tetrahydro-beta-carboline

Product 1

HCID 155992912,3,4,9-tetrahydro-2-[2-(2-pyridinyl)ethyl]-1H-pyrido[3,4-b]indoleYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1.72 g., 0.01 mol), 2-vinylpyridine (1.0 g., 0.01 mol) and 2 ml. of glacial acetic acid were refluxed in 25 ml. of methanol for 24 hours. The solvent was removed in vacuo and the separated solid was suspended in water. The solution was made slightly basic via the addition of solid potassium carbonate and it was extracted with methylene chloride (4×150 ml.). The methylene chloride layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford 1.2 g. (44% yield) of 2,3,4,9-tetrahydro-2-[2-(2-pyridinyl)ethyl]-1H-pyrido[3,4-b]indole. This intermediate was dissolved in 50 ml. of dimethylformamide and 0.92 g. (0.04 mol) of sodium hydride was added and stirring was continued for 1 hour. To the stirred solution 0.66 g. (0.004 mol) of benzyl bromide was added and the reaction mixture was stirred at room temperature overnight. The solvent was removed under vacuum and the solid residue was suspended in water and extracted with methylene chloride (3×100 ml.). The organic layer was separated, dried and evaporated. The remaining oil was dissolved in ethanol and converted to the dihydrochloride salt; mp 278°-280° C.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe solution was made slightly basic via the addition of solid potassium carbonate and it
  3. extractionwas extracted with methylene chloride (4×150 ml.)
  4. dry with materialThe methylene chloride layer was dried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customto afford 1.2 g

Sources & evidence

ORD record
ord-8da31f816fe94b41bb05d3a84e5b9363
Source dataset
uspto-grants-1988_06
Patent number
US04754038

Reaction notes

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