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

HRID 980315Notes

Reaction equation

HRID 980315 reaction equation
[CH2:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3][NH:2]1.Br.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1CCCBr.N1C=CC=[CH:27][C:26]=1[CH2:31]CCCBr.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[N:15]1[CH:16]=[CH:17][CH:18]=[C:19]([CH2:27][CH2:26][CH2:31][N:2]2[CH2:3][CH2:4][C:5]3[NH:6][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=4[C:13]=3[CH2:1]2)[CH:20]=1

Participants

5

Reactant 4

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 7232301H,2H,3H,4H,5H-pyrido[4,3-b]indoleHCID 534063864-Pyridinylbutyl bromideHCID 679377483-Pyridinylpropyl bromide hydrobromide

Product 1

HCID 137724482,3,4,5-Tetrahydro-2-[3-(3-pyridinyl)propyl]-1H-pyrido[4,3-b]indole

Procedure

The title compound was prepared following the procedure of Example 1 with the exception 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 and 3-pyridinylpropyl bromide hydrobromide replaced the 4-pyridinylbutyl bromide salt. The product was converted to the dihydrochloride salt; mp 223°-225° C.

Sources & evidence

ORD record
ord-9ae7cce3fd4b478daa52dd4efb45c599
Source dataset
uspto-grants-1987_01
Patent number
US04636563

Reaction notes

Loading…