1-(4-Bromophenethyl)pyrrolidine → HCID 22266698, compound

HRID 489547Notes

Reaction equation

HRID 489547 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:24](=[O:25])[NH:23][CH2:22][CH2:21][C:20]=2[C:19]=34)=[CH:8][CH:7]=1)[CH3:2].BrC1C=CC(CCN2CCCC2)=CC=1>>[N:3]1([CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[NH:13][C:14]4[CH:15]=[CH:16][CH:17]=[C:18]5[C:24](=[O:25])[NH:23][CH2:22][CH2:21][C:20]=3[C:19]=45)=[CH:8][CH:7]=2)[CH2:1][CH2:2][CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 121778101-(4-Bromophenethyl)pyrrolidineHCID 222666792-[4-(2-Diethylamino-ethyl)-phenyl]-3,4,5,6-tetrahydro-azepino[5,4,3-cd]indol-6-one

Product 1

HCID 22266698HCID 22266698, compound

Procedure

In a manner similar to that described for 2-[4-(2-diethylamino-ethyl)-phenyl]-3,4,5,6-tetrahydro-azepino[5,4,3-cd]indol-6-one (Example YY), the tricyclic bromide (198 mg, 0.75 mmol) and 1-[2-(4-bromo-phenyl)-ethyl]-pyrrolidine were coupled to yield 2-[4-(2-pyrrolidin-1-yl-ethyl)-phenyl]-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 160 mg (59%) as a beige solid: m.p. 228-229° C. (dec); 1H NMR (300 MHz, d6-DMSO) δ 1.69 (m, 4H), 2.51 (m, 4H), 2.67 (m, 2H), 2.81 (m, 2H), 3.05 (m, 2H), 3.39 (m, 2H), 7.20 (t, J=7.8 Hz, 1H), 7.39 (d, J=8.1 Hz, 2H), 7.56 (m, 3H), 7.68 (d, J=7.5 Hz, 1H), 8.08 (br t, 1H), 11.31 (br s, 1H). MS (FAB, MH+): 360. Anal. (C23H25N3O) C, H, N.

Sources & evidence

ORD record
ord-be0031bbe5774bdfb0e695a3e9dc973d
Source dataset
uspto-grants-2005_12
Patent number
US06977298B2

Reaction notes

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