Ammonia → (6bR,10aS)-8-[3-(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 1789958Notes

Reaction equation

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

Participants

Reactant 3

HCID 222Ammonia

HCID 21302499Ihch-7113

HCID 220368133-(3-Chloropropyl)-1,2-benzisoxazole

Product 1

HCID 10287923(6bR,10aS)-8-[3-(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 3-(3-chloropropyl)-1,2-benzisoxazole from Step D Example 22 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 the General procedure A of Example 197. 1H NMR (300 MHz, CDCl3) δ 7.59–7.62 (m, 1H), 7.46–7.50 (m, 2H), 7.20–7.25 (m, 1H), 6.57 (dd, J=7.7 Hz, 7.3 Hz, 1H), 6.43 (d, J=6.9 Hz, 1H), 6.33 (d, J=7.3 Hz), 3.48–3.52 (m, 1H), 3.06–3.25 (m, 4H), 2.94–2.99 (m, 2H), 2.70–2.89 (m, 4H), 2.79 (s, 3H), 2.20–2.65 (m, 3H), 1.92–2.07 (m, 4H) ppm. MS (CI, NH3) m/e 389 (base, M+H+).

Sources & evidence

ORD record: ord-df231b2eefe7403fa727fe476aa6064d
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071186B2

Reaction notes

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