Sodium Hydroxide → HCID 10309281, compound

HRID 350797Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C@@H:21]3[CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][C@@H:20]3[N:13]3[CH2:14][CH2:15][N:16]([CH3:19])[C:17]([CH:18]=1)=[C:12]23.[OH-].[Na+]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C@@H:21]3[CH2:22][NH:23][CH2:24][CH2:25][C@@H:20]3[N:13]3[CH2:14][CH2:15][N:16]([CH3:19])[C:17]([CH:18]=1)=[C:12]23

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 86591145HCID 86591145, compound

Product 1

HCID 10309281HCID 10309281, compoundYield 80%

Procedure

The hydrochloride salt of the title compound was prepared from tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (50 mg) using the deprotection procedures described in Example 275, Step B. The salt formed was free-based with 6 N NaOH to give the title compound (31 mg, 80%). 1H NMR (CD3OD, 300 MHz) δ 1.80–1.90 (m, 1H), 1.96–2.10 (m, 1H), 2.50 (m, 2H), 2.76–2.90 (m, 5H), 2.93–3.1 (m, 2H), 3.20–3.50 (m, 4H), 3.50–3.60 (m, 2H), 6.40 (d, 1H), 6.5 (d, 1H), 7.22–7.32 (m, 2H), 7.44 (d, 1H) ppm. MS-CI m/z=374 [C20H21Cl2N3+H]+

Workup

customThe salt formed

Sources & evidence

ORD record: ord-d701a2ffc1724c1ba856d2259d30e422
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183282B2

Reaction notes

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