Piperidine → HCID 57809291, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH3:16])[C:8]([OH:10])=O)[CH3:2].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:6]=[C:7]([C:8]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:10])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH3:16])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-ethoxy isopthalic acid 3-ethyl ester (600 mg, 2.5 mmol) in 10 mL of acetonitrile was added piperidine (429 mg, 5.0 mmol). The resulting mixture was cooled to 0° C. To this solution was added HBTU (1.4 g, 3.78 mmol, in 5 mL of acetonitrile) followed by N,N-diisopropylethylamine (2.2 mL, 12.6 mmol). The reaction was allowed to stir overnight at room temperature. The reaction mixture was concentrated in vacuo. The residue was diluted with 10% potassium carbonate and extracted with methylene chloride. The organic extract was concentrated and purification of the crude residue by flash column chromatography (silica gel, eluting with a gradient of ethyl acetate in hexanes) gave 632 mg (2.07 mmol, 82%) of pure 2-ethoxy-5-(piperidine-1-carbonyl)-benzoic acid ethyl ester. LC-MS: 306.3 [(M+H)+].
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additionThe residue was diluted with 10% potassium carbonate
- extractionextracted with methylene chloride
- extractionThe organic extract
- concentrationwas concentrated
- custompurification of the crude residue by flash column chromatography (silica gel
- washeluting with a gradient of ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-fbedc33ba66147e6ac1f5d46bed54f8e
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07579368B2
Reaction notes
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