Hydrochloric Acid → HCID 22129660, compound

HRID 1857656Notes

Reaction equation

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

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of N-[2-(3,4-dichlorophenyl)-2-pyrrolidin-1-yl-ethyl]benzamide (260 mg) in dimethylsulfoxide (1.5 mL) and methyl iodide (230 mg) were added to a solution of KOH (190 mg) in dimethylsulfoxide (0.7 mL). The reaction was stirred at 23° C. for 3/4 hour, was poured into water (10 mL), and extracted with dichloromethane (20 mL). The organic layer was washed (brine), dried and evaporated to a gold oil. Chromatography, with ethyl acetate:hexane (50:50 then 75:25) as the eluent, gave an oil, which was dissolved in diethylether and treated with hydrochloric acid (g)/diethylether to provide the title compound as a white solid (60 mg); mp 199-202° C.; MS: m/z=377(M+1); NMR: 1.98 (m,1), 2.12 (m,2), 2.35 (m,1), 2.54 (s,3,), 2.61 (m,1), 3.35 (m,2), 3.88 (t,1), 4.13 (m,1), 4.63 (m,2), 7.2 (dd,1), 7.26 (s,1), 7.53 (d,1), 7.79 (broad s,1), 8.11 (broad s,1), 13.23 (broad s,1). Analysis Calculated: C, 57.43; H, 5.6; N, 6.7; Found: C, 57.59; H, 5.61; N, 6.35.

Workup

extractionextracted with dichloromethane (20 mL)
washThe organic layer was washed (brine)
customdried
customevaporated to a gold oil
customChromatography, with ethyl acetate:hexane (50:50 then 75:25) as the eluent, gave an oil, which

Sources & evidence

ORD record: ord-b729e409801240a9baa575ae6aa60ee8
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147083

Reaction notes

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