4-Piperidinecarboxylic acid → 1-(4-fluorobenzoyl)piperidine-4-carboxylic acid

HRID 2082304Notes

Reaction equation

HRID 2082304 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>O.C(Cl)Cl>[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([N:1]2[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]2)=[O:22])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 11430Potassium CarbonateHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 7780751-(4-fluorobenzoyl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Piperidine-4-carboxylic acid (25.8 g, 200 mmol) and potassium carbonate (82.9 g, 600 mmol) are combined in water (500 mL) and methylene chloride (1 L) at 0° C. 4-Fluorobenzoyl chloride (31.7 g, 200 mmol) is dissolved in methylene chloride (200 mL) and added to the first mixture dropwise over 45 min. The mixture is stirred for 2 hr, after which the aqueous layer is separated and acidified to pH 1.5 with concentrated HCl. The aqueous mixture is extracted three times with methylene chloride, and the organic extracts are dried over magnesium sulfate and evaporated to give the title compound.

Workup

  1. customat 0° C
  2. additionadded to the first mixture dropwise over 45 min
  3. customafter which the aqueous layer is separated
  4. extractionThe aqueous mixture is extracted three times with methylene chloride
  5. dry with materialthe organic extracts are dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-225a4f98bc1e4ad995ade352ac6d4b43
Source dataset
uspto-grants-1993_02
Patent number
US05189036

Reaction notes

Loading…