3,4,5-Trimethoxybenzoic Acid → HCID 68681026, compound
Reaction equation
[CH3:1][C:2](=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[C:25](O)=[O:26].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CO.C(Cl)(Cl)Cl>[CH3:34][O:33][C:29]1[CH:28]=[C:24]([CH:23]=[C:22]([O:21][CH3:20])[C:30]=1[O:31][CH3:32])[C:25]([N:4]([CH2:3][C:2]([CH3:1])=[CH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:26]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
(2-Methyl-3-phenyl-allyl)-(2-piperidin-1-yl-ethyl)-amine, 0.5 g (1.9 mmol), was dissolved in 10 ml of anhydrous methanol under nitrogen. The solution was cooled to 0° C. To this mixture was added 3,4,5-trimethoxybenzoic acid 0.49 g (2.3 mmol), 0.2 ml of triethylamine, and TBTU 1.2 g (3.8 mmol). The reaction was stirred for 18 hours at room temperature. The reaction mixture was then diluted with chloroform, extracted with 2×10 ml of water, 2×10 ml sodium bicarbonate, and washed 2×10 ml of brine. The organic layer was dried over sodium sulfate and was concentrated. The compound was then purified on silica gel using 1.2% methanol in chloroform to give 102 mg of product as an off white HCl salt. Yield: 12%.
Workup
- extractionextracted with 2×10 ml of water, 2×10 ml sodium bicarbonate
- washwashed 2×10 ml of brine
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationwas concentrated
- customThe compound was then purified on silica gel using 1.2% methanol in chloroform
Sources & evidence
- ORD record
- ord-c62232a32fdb4db0ab1d99937b1a9a45
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07649011B2
Reaction notes
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