Acetic Acid → HCID 11332725, compound
Reaction equation
F[C:2](F)(F)[C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)C=[CH:7][CH:8]=1.CO.C(O)(=[O:21])C>C(OCC)(=O)C>[CH:13]1[C:14]2[C:9](=[CH:5][CH:4]=[C:3]([CH2:8][CH:7]=[O:21])[CH:2]=2)[CH:10]=[CH:11][N:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2.5 °C
Procedure
1.75 g (0.0077 mol) of 4-(3-(trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine, 30 ml of methanol, 1.15 ml of glacial acetic acid and 0.73 g of anhydrous ethyl acetate are mixed. The mixture is cooled to 0-5° C. and 1.14 g of 7-isoquinolylacetaldehyde (as obtained according to the Preparation) and, with care, 1.1 g (0.0175 mol) of sodium cyanoborohydride are added thereto. The mixture is stirred at 0-5° C. for 1.5 hours and subsequently at ambient temperature overnight. 7 ml of concentrated hydrochloric acid are added, the mixture is stirred for 10 minutes, the solvent is evaporated under reduced pressure and the residue is taken up in an ethyl acetate/dilute NH4OH mixture. The organic phase is dried over sodium sulfate and filtered, and the solvent is evaporated. The residue is purified on a column of silica gel, elution being carried out with an ethyl acetate/methanol=9/1 mixture. The title compound is obtained. The dihydrochloride is prepared using a solution of isopropanol saturated with hydrochloric acid. 1.1 g of product are obtained.
Sources & evidence
- ORD record
- ord-c0d0fb381b5a45c296134649a0435491
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07326720B2
Reaction notes
Loading…