Sodium Hydroxide → HCID 58137328, compound

HRID 1424571Notes

Reaction equation

HRID 1424571 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][C:11]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]([O:17]CC)=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][C:11]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]([OH:17])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58137305HCID 58137305, compound

Product 1

HCID 58137328HCID 58137328, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-benzoyl-3-benzylpiperidine-3-carboxylate (6.308 g; 18 mmol) was hydrolyzed with 1 N aq NaOH (220 mL) in ethanol (110 mL) for 20 h at rt. The ethanol was removed by rotary evaporation and the aqueous layer was extracted once with CH2Cl2. The pH of the aqueous layer was adjusted to pH=3-4 with 1 N aq HCl and extracted with CH2Cl2 (3×). The organic phase was dried over anhydrous Na2SO4, filtered and evaporated to give 1-benzoyl-3-benzylpiperidine-3-carboxylic acid (3.24 g, 55.7%). 1H NMR (CD3OD, 400 MHZ): δ=1.12 (m, 3H), 1.50˜1.72 (m, 4H), 2.18 (m, 1H), 2.75 (d, 1H), 3.05 (m, 1H), 3.16 (m, 1H), 4.08 (m, 2H), 7.08 (m, 2H), 7.22 (m, 3H), 7.48 (m, 5H).

Workup

  1. customThe ethanol was removed by rotary evaporation
  2. extractionthe aqueous layer was extracted once with CH2Cl2
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3f321ffda39b457eabbe74392d8af193
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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