Ammonia → 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-pyridinyl)-1-butanone hydrochloride

HRID 1764797Notes

Reaction equation

HRID 1764797 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:6].[CH3:13][N:14]1[C:23]2[CH:22]=[CH:21][CH:20]=[C:19]3[CH:24]4[CH2:29][NH:28][CH2:27][CH2:26][CH:25]4[N:17]([C:18]=23)[CH2:16][CH2:15]1.N>>[ClH:1].[CH3:13][N:14]1[C:23]2[CH:22]=[CH:21][CH:20]=[C:19]3[C@@H:24]4[CH2:29][N:28]([CH2:2][CH2:3][CH2:4][C:5]([C:7]5[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=5)=[O:6])[CH2:27][CH2:26][C@@H:25]4[N:17]([C:18]=23)[CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 101769713-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalineHCID 124710044-Chloro-1-(4-pyridinyl)-1-butanone

Product 1

HCID 102163474-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-pyridinyl)-1-butanone hydrochloride

Procedure

The title compound was prepared from addition of the of 4-chloro-1-(4-pyridyl)butan-1-one to 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 of Example 197. 1H NMR (300 MHz, CDCl3) δ 8.79 (dd, J=4.4 Hz, 1.8 Hz, 2H), 7.74 (dd, J=4.4 Hz, 1.4 Hz, 2H), 6.64 (dd, J=7.4 Hz, 7.6 Hz, 1H),6.49 (d, J=6.9 Hz, 1H), 6.39 (d, J=7.7 Hz, 1H), 3.54-3.62 (m, 1H), 3.23-3.31 (m, 2H), 3.13-3.17 (m, 1H), 2.95-3.03 (m, 2H), 2.85 (s, 3H), 2.76-2.84 (m, 2H), 2.57-2.60 (m, 1H), 2.31-2.41 (m, 1H), 2.22 (td, J=11.7 Hz, 2.9 Hz, 1H), 1.92-2.02 (m, 3H), 1.83-1.88 (m, 1H), 1.66-1.76 (m, 2H) ppm. MS (CI, NH3) m/e 376 (base, M+H+).

Sources & evidence

ORD record
ord-2acfa28b93034bc48cfd7504c605efc2
Source dataset
uspto-grants-2007_06
Patent number
USRE039680E1

Reaction notes

Loading…