Tetrafluoro-m-phenylenediamine dihydrochloride → 4-Phenethyl-1-(2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)piperazin-2-one dihydrochloride

HRID 2365405Notes

Reaction equation

HRID 2365405 reaction equation
[O:1]=[C:2]1[CH2:7][N:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4][N:3]1[C:16]1[CH:17]=[CH:18][C:19]2[C:20]3[CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25][C:21]=3[NH:22][C:23]=2[CH:24]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:48].Cl>>[ClH:48].[ClH:48].[CH2:8]([N:6]1[CH2:5][CH2:4][N:3]([C:16]2[CH:17]=[CH:18][C:19]3[C:20]4[CH2:28][NH:27][CH2:26][CH2:25][C:21]=4[NH:22][C:23]=3[CH:24]=2)[C:2](=[O:1])[CH2:7]1)[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 67986821tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 679696904-Phenethyl-1-(2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)piperazin-2-one dihydrochlorideYield 73%

Procedure

tert-Butyl 7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (160 mg, 0.337 mmol) was deprotected and converted to the dihydrochloride salt according to Example 2 (step f) to provide the title compound (110 mg, 73%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 11.35 (s, 1H), 9.35 (s, 2H), 7.49 (d, J=8.3 Hz, 1H), 7.41-7.23 (m, 6H), 6.97-6.94 (dd, J=8.3, 1.7 Hz, 1H), 4.30 (s, 2H), 4.24-3.97 (m, 3H), 3.96-3.73 (m, 2H), 3.63-3.27 (m, 5H), 3.23-3.08 (m, 2H), 3.08-2.98 (m, 2H); ESI MS m/z 375 [M+H]+; HPLC (Method B) 98.8% (AUC), tR=11.2 min.

Sources & evidence

ORD record
ord-24bd83b6abe24855a9c4266efd7bb82b
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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