4-Fluorobenzoic Acid → HCID 18919757, compound

HRID 1291182Notes

Reaction equation

HRID 1291182 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([O:13][CH:10]2[CH2:9][CH2:8][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:15][CH:14]=3)[CH2:12][CH2:11]2)=[O:31])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 99734-Fluorobenzoic AcidHCID 218852-DimethylaminopyridineHCID 764482HCID 764482, compoundHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18919757HCID 18919757, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.226 g (0.001 mol) of 1-(4-chloro-benzyl)-piperidin-4-ol was dissolved in 5 ml of dimethylformamide and treated with 0.061 g (0.0005 mol) of dimethylaminopyridine and 0.14 g (0.001 mol) of 4-fluoro-benzoic acid. The mixture was cooled to 0° and 0.211 g (0.0011 mol) of N-ethyl-N'-(3-dimethylamino-propyl)-carbodiimide hydrochloride was added. The mixture was warmed to room temperature and stirred for 72 hrs. The solvent was distilled off and the residue was taken up in ethyl acetate and treated with silica gel. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane (1:2) as the eluent. 0.29 g (83%) of 1-(4-chloro-benzyl)-piperidin-4-yl 4-fluoro-benzoate was obtained as a colorless oil.

Workup

  1. temperatureThe mixture was cooled to 0°
  2. distillationThe solvent was distilled off
  3. additiontreated with silica gel
  4. customAfter removal of the solvent the residue
  5. customwas chromatographed on silica gel with ethyl acetate/hexane (1:2) as the eluent

Sources & evidence

ORD record
ord-ba0205ade6cd4d8aae1a378b7fd2d5bb
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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