1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → ethyl 1-(1H-indole-2-carbonyl)piperidine-4-carboxylate
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:43]1[CH2:48][CH2:47][CH:46]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:45][CH2:44]1>C1COCC1.O.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([N:43]1[CH2:48][CH2:47][CH:46]([C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:45][CH2:44]1)=[O:12]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
1H-indole-2-carboxylic acid (2.49 g, 15.45 mmol), EDCI (4.44 g, 23.18 mmol), and HOBT (3.55 g, 23.18 mmol) were dissolved in THF (Volume: 30.0 ml). The reaction was allowed to stir for 15 minutes before DIEA (4.05 ml, 23.18 mmol) and ethyl piperidine-4-carboxylate (3.57 ml, 23.18 mmol) were added to the reaction. The reaction was diluted with water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, 1H HCl, and saturated sodium chloride. The organic layer was then dried over magnesium sulfate, filtered and concentrated. the resulting solid is then triturated with ethyl acetate. (Yield: 3.27 g, white solid) 1H-NMR (400 MHz, DMSO-d6) 11.55, 7.60, 7.41, 7.18, 7.04, 6.77, 4.40-4.27, 4.09, 3.18, 2.76-2.63, 1.97-1.88, 1.65-1.51, 1.20
Workup
- additionwere added to the reaction
- washThe organic layer was washed with saturated sodium bicarbonate, 1H HCl, and saturated sodium chloride
- dry with materialThe organic layer was then dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customthe resulting solid is then triturated with ethyl acetate
Sources & evidence
- ORD record
- ord-016e0bbf2c4d467488e5112edd4b84a3
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846684B2
Reaction notes
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