Sodium Carbonate → 1-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)piperidine

HRID 323254Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][CH2:16][OH:17])[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[Na+].[Na+].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:29](Cl)=[O:30]>C(OCC)(=O)C.O>[CH3:38][O:37][C:33]1[CH:32]=[C:28]([CH:27]=[C:26]([O:25][CH3:24])[C:34]=1[O:35][CH3:36])[C:29]([N:11]1[CH2:12][CH2:13][CH2:14][C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)([CH2:15][CH2:16][OH:17])[CH2:10]1)=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

Combine 3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)piperidine (1.08 g, 3.94 mmol) and sodium carbonate (0.21 g, 2.00 mmol) in 1/1 ethyl acetate/water (50 mL). Cool the reaction mixture to 0° C. with an ice bath. Add 3,4,5-trimethoxybenzoyl chloride (0.83 g, 3.58 mmol). Warm to ambient temperature. After 18 hours, separate the layers and extract the aqueous layer three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel to give the title compound: Rf=0.5 (silica gel, 1/1 ethyl acetate/hexane). Elemental Analysis calculated for C23H27Cl2NO5: C 58.97; H 5.81; N 2.99; Found C 58.85; H 5.90; N 2.96.

Workup

temperatureWarm to ambient temperature
customseparate the layers
extractionextract the aqueous layer three times with ethyl acetate
dry with materialDry the combined organic layers over Na2SO4
filtrationfilter
concentrationconcentrate in vacuo
customto obtain a residue

Sources & evidence

ORD record: ord-6ceae20135db4b2dbae96572f29feaca
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211199B1

Reaction notes

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