Acetic Acid → 8-Fluoro-5-(4-fluorophenyl)-2,3,4,5-tetrahydro-2-[2-(2-pyridinyl) ethyl]-1H-pyrido[4,3-b]indole

HRID 652473Notes

Reaction equation

HRID 652473 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]3[CH2:18][CH2:19][NH:20][CH2:21][C:5]=3[C:4]=2[CH:3]=1.[CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)=[CH2:23].C(O)(=O)C>CO>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[C:6]3[CH2:18][CH2:19][N:20]([CH2:23][CH2:22][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:21][C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 75212-VinylpyridineHCID 126299068-fluoro-5-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 139003928-Fluoro-5-(4-fluorophenyl)-2,3,4,5-tetrahydro-2-[2-(2-pyridinyl) ethyl]-1H-pyrido[4,3-b]indoleYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 8-fluoro-5-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (3 g, 0.01 mole), 2-vinylpyridine (1.7 g, 0.01 mol) and 2 mL of glacial acetic acid were refluxed for 48 hours in 30 mL of methanol. The solvent was removed in vacuo and the separated solid was purified by HPLC using ethyl acetate as the eluant to afford 3.5 g (89.9% yield) of the title compound. It was converted to the dihydrochloride salt; mp. 267°-270° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe separated solid was purified by HPLC

Sources & evidence

ORD record
ord-3e53e422c9604183b68682d105ec72ec
Source dataset
uspto-grants-1987_06
Patent number
US04672117

Reaction notes

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