Ammonia → (6bR,10aS)-8-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline hydrochloride

HRID 350784Notes

Reaction equation

HRID 350784 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[C:9]2[CH:10]=[CH:11][C:12]([F:14])=[CH:13][C:8]=2[O:7][N:6]=1.[CH3:15][N:16]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]3[C@@H:26]4[CH2:31][NH:30][CH2:29][CH2:28][C@@H:27]4[N:19]([C:20]=23)[CH2:18][CH2:17]1.N>>[ClH:1].[F:14][C:12]1[CH:11]=[CH:10][C:9]2[C:5]([CH2:4][CH2:3][CH2:2][N:30]3[CH2:29][CH2:28][C@@H:27]4[N:19]5[C:20]6[C:21]([C@@H:26]4[CH2:31]3)=[CH:22][CH:23]=[CH:24][C:25]=6[N:16]([CH3:15])[CH2:17][CH2:18]5)=[N:6][O:7][C:8]=2[CH:13]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazoleHCID 21302499Ihch-7113

Product 1

HCID 10151425(6bR,10aS)-8-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline hydrochloride

Procedure

The title compound was prepared from addition of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole from Step D and (6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline following General procedure A, Example 197. 1H NMR (300 MHz, CDCl3) δ 7.63 (dd, J=8.8 Hz, 4.7 Hz, 1H), 7.20–7.24 (m, 1H), 7.03–7.10 (m, 1H), 6.65 (dd, J=7.7 Hz, 7.7 Hz, 1H), 6.50 (d, J=7.3 Hz, 1H), 6.41 (d, J=7.3 Hz), 3.73–3.77 (m, 1H), 3.55–3.62 (m, 1H), 3.21–3.32 (m, 3H), 2.91–3.10 (m, 3H), 2.86 (s, 3H), 2.75–2.82 (m, 2H), 2.54–2.63 (m, 1H), 2.41–2.48 (m, 1H), 1.95–2.11 (m, 6H) ppm. MS (CI, NH3) m/e 407 (base, M+H+).

Sources & evidence

ORD record
ord-67f255bbed3f41228a5811f7b02a8ff6
Source dataset
uspto-grants-2007_02
Patent number
US07183282B2

Reaction notes

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