Tetrafluoro-m-phenylenediamine dihydrochloride → 8-Chloro-2,3,4,5-tetrahydro-2-[3-(2-pyridinyl)-propyl]-1H-pyrido[4,3-b]indole

HRID 980317Notes

Reaction equation

HRID 980317 reaction equation
Br.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10]Br.[Cl:12][C:13]1[CH:21]=[CH:20][C:19]2[NH:18][C:17]3[CH2:22][CH2:23][NH:24][CH2:25][C:16]=3[C:15]=2[CH:14]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[Cl:12][C:13]1[CH:21]=[CH:20][C:19]2[NH:18][C:17]3[CH2:22][CH2:23][N:24]([CH2:10][CH2:9][CH2:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=4)[CH2:25][C:16]=3[C:15]=2[CH:14]=1

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 9049708-Chloro-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indoleHCID 679377483-Pyridinylpropyl bromide hydrobromide

Product 1

HCID 137724578-Chloro-2,3,4,5-tetrahydro-2-[3-(2-pyridinyl)-propyl]-1H-pyrido[4,3-b]indole

Procedure

The title compound was prepared following the procedure of Example 1 with the exception that 3-pyridinylpropyl bromide hydrobromide was used instead of 4-pyridinylbutyl bromide hydrobromide and 8-chloro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole was used instead of 8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. The product as converted to the dihydrochloride salt; mp. 240°-242° C.

Sources & evidence

ORD record
ord-f4fa169be3394a23840d269872810f8e
Source dataset
uspto-grants-1987_01
Patent number
US04636563

Reaction notes

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