Lithium Hydroxide → HCID 28398271, compound

HRID 83638Notes

Reaction equation

HRID 83638 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]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]1)=[O:11].[OH-].[Li+]>C1COCC1.O>[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:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1)=[O:11]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68380075ethyl 1-(1H-indole-2-carbonyl)piperidine-4-carboxylate

Product 1

HCID 28398271HCID 28398271, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

ethyl 1-(1H-indole-2-carbonyl)piperidine-4-carboxylate (3.0 g, 9.99 mmol) and lithium hydroxide, H2O (4.19 g, 100 mmol)) were dissolved in THF (Ratio: 1, Volume: 20 ml) and Water (Ratio: 2, Volume: 40.0 ml) and allowed to stir overnight at room temperature. The reaction was diluted with water, and extracted with diethyl ether. The aqueous layer was acidified using 2N HCl to pH ˜2. A fine, white suspension resulted. The aqueous layer was extracted with ethyl acetate twice. The combined ethyl acetate layers were dried over magnesium sulfate, filtered and concentrated to afford the product as a white solid. (Yield: 678 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 12.33, 11.53, 7.60, 7.41, 7.21-6.94, 6.76, 4.40-4.21, 3.17, 2.66-2.53, 1.97-1.82, 1.63-1.47

Workup

  1. extractionextracted with diethyl ether
  2. customA fine, white suspension resulted
  3. extractionThe aqueous layer was extracted with ethyl acetate twice
  4. dry with materialThe combined ethyl acetate layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8dd3bdfdc97481b96b8f0b831e20498
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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