Sodium Iodide → 3-[3-Chloro-6-(3-dimethylamino-propoxy)-benzo[b]thiophen-2-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt

HRID 1173834Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:4]=2[S:5][C:6]=1[CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]1=[O:19].Cl.Br[CH2:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>>[ClH:1].[Cl:1][C:2]1[C:3]2[CH:23]=[CH:22][C:21]([O:24][CH2:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])=[CH:20][C:4]=2[S:5][C:6]=1[CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[C:9]1=[O:19]

Participants

Reactant 4

HCID 5238Sodium Iodide

HCID 10796Cesium carbonate

HCID 117103063-(3-Chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one

HCID 12440776(3-Bromo-propyl)-dimethyl-amine hydrochloride

Product 1

HCID 117128103-[3-Chloro-6-(3-dimethylamino-propoxy)-benzo[b]thiophen-2-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt

Procedure

Using the procedure to synthesize Example 12 and using reagents 3-(3-chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one (150 mg, 0.412 mmol), (3-bromo-propyl)-dimethyl-amine hydrochloride (167 mg, 0.824 mmol), sodium iodide (62 mg, 0.412 mmol), and cesium carbonate (1.07 g, 3.30 mmol) afford the freebase of the title compound. Dissolve freebase in dichloromethane (5 mL) and add HCl in ether (2M, 0.4 mL), concentrate to give title compound (105 mg, 52%) as a yellow solid: Mass spectrum (apci) m/z=449.3 (M+H).

Workup

customto synthesize Example 12

Sources & evidence

ORD record: ord-6dd880a8ec774983a6223b7864b974f6
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834194B2

Reaction notes

Loading…