4-Fluorobenzoic Acid → HCID 18919845, compound

HRID 1291184Notes

Reaction equation

HRID 1291184 reaction equation
[Br: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]([Br: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 677772HCID 677772, compoundHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18919845HCID 18919845, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.428 g (0.00184 mol) of 1-(4-bromo-benzyl)-piperidin-4-ol was dissolved in 8 ml of dimethylformamide and treated with 0.097 g (0.00079 mol) of dimethylaminopyridine and 0.222 g (0.00158 mol) of 4-fluoro-benzoic acid. The mixture was cooled to 0° and 0.334 g (0.00174 mol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride was added. The mixture was warmed to room temperature and stirred for 18 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. 0.47 g (76%) of 1-(4-bromo-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-bcf710ee93bb47e7aaaf5f6199a0ae6b
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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