Butyl bromide → HCID 86593172, compound

HRID 1292911Notes

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16]3=[C:17]([C@H:19]4[CH2:24][NH:23][CH2:22][CH2:21][C@H:20]4[N:15]3[CH2:14][CH2:13][CH2:12]2)[CH:18]=1.Br[CH2:26][CH2:27][CH2:28][CH3:29]>>[CH2:26]([N:23]1[CH2:22][CH2:21][C@H:20]2[N:15]3[C:16]4[C:11](=[CH:10][C:9]([C:3]5[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=5[Cl:1])=[CH:18][C:17]=4[C@H:19]2[CH2:24]1)[CH2:12][CH2:13][CH2:14]3)[CH2:27][CH2:28][CH3:29]

Participants

Reactant 2

HCID 8002Butyl bromide

HCID 10109086HCID 10109086, compound

Product 1

HCID 86593172HCID 86593172, compound

Procedure

The title compound was prepared by the method of Example 382 as a yellow oil (28 mg, 82%) from (±)-cis-2-(2,3-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol) and 1-bromobutane (23 mg, 0.17 mmol). 1H NMR (CDCl3, 300 MHz) δ 0.92(t, J=7.3 Hz, 3H), 1.32 (se, J=7.3 Hz, 2H), 1.53-1.65 (br, 2H), 2.02-2.25 (m, 5H), 2.38-2.53 (br, 2H), 2.58-2.68 (m, 1H), 2.75 (t, J=6.4 Hz, 2H), 2.80-2.92 (br, 1H), 2.95-3.07 (br, 1H), 3.31 (dt, J=10.3, 3.6 Hz, 1H), 3.37-3.45 (br, 2H), 6.94 (s, 1H), 6.99 (s, 1H), 7.15-7.21 (m, 2H), 7.35-7.40 (m, 1H) ppm.

Sources & evidence

ORD record: ord-c416fe0e2ccf4817812219b8caa76131
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238690B2

Reaction notes

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