Hydrochloric Acid → 2-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acid

HRID 713425Notes

Reaction equation

HRID 713425 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([O:17]CC)=[O:16])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C.O>[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71227338Ethyl 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetate

Product 1

HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidYield 99.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(4-(4-Fluorobenzoyl)piperidin-1-yl)acetate (52.7 g, 180 mmol) in ethanol (300 mL) was added sodium hydroxide solution in water (1.8 M, 300 mL). The mixture was stirred at ambient temperature for 24 h then neutralized with HCl (37%) until pH 5˜7. The solvent was evaporated under reduced pressure, dissolved with methanol and methylene chloride, and filtered. The resulting solution was evaporated to give the title compound as a white solid (47.7 g, >99% yield). 1H NMR (400 MHz, CD3OD) δ 8.11 (dd, J=8.8, 5.3 Hz, 2H), 7.26 (t, J=8.8 Hz, 2H), 3.57-3.85 (m, 5H), 3.21 (t, J=11.0 Hz, 2H), 1.96-2.18 (m, 4H). MS m/z 266.3 (M+1), retention time=0.87 min.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutiondissolved with methanol and methylene chloride
  3. filtrationfiltered
  4. customThe resulting solution was evaporated

Sources & evidence

ORD record
ord-326cc96c837f411995da44d7f11c4912
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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