Ammonia → HCID 69437489, compound

HRID 1793549Notes

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][CH:29]=[CH2:30].N>>[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][N:23]([CH2:30][CH2:29][CH2:28][CH:27]=[CH2:26])[CH2:22][CH2:21][C@@H:20]4[N:15]3[CH2:14][CH2:13][CH2:12]2)[CH:18]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 707041-Pentene, 5-bromo-

HCID 20576931HCID 20576931, compound

Product 1

HCID 69437489HCID 69437489, compound

Procedure

The title compound was prepared by the method of Example 382 as a yellow oil (22 mg, 62%) from (7aS,11aR)-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 5-bromo-1-pentene (25 mg, 0.17 mmol). 1H NMR (CDCl3, 300 MHz) δ 1.62–1.75 (br, 2H), 2.01–2.22 (m, 7H), 2.35–2.53 (br, 3H), 2.58–2.65 (m, 1H), 2.74 (t, J=6.6 Hz, 2H), 2.75–2.85 (br, 1H), 2.88–3.05 (br, 1H), 3.28–3.41 (m, 3H), 4.97 (d, J=13.5 Hz, 1H), 5.02 (dd, J=17.6, 1.5 Hz, 1H), 5.73–5.83 (m, 1H), 6.93 (s, 1H), 6.98 (s, 1H), 7.15–7.21 (m, 2H), 7.36–7.40 (m, 1H) ppm. MS (CI, NH3): 427.1 (base, M+H).

Sources & evidence

ORD record: ord-ef5abb8dd2e24110a885b643ecab8627
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07081455B2

Reaction notes

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