Benzoyl chloride → HCID 18919738, compound

HRID 1291155Notes

Reaction equation

HRID 1291155 reaction equation
[F: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.C(N(CC)CC)C.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[C:23]([O:13][CH:10]1[CH2:9][CH2:8][N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 765229HCID 765229, compound

Product 1

HCID 18919738HCID 18919738, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.63 g (0.003 mol) of 1-(4-fluoro-benzyl)-piperidin-4-ol and 2.09 ml (0.015 mol) of triethylamine were dissolved in 30 ml of toluene, treated with 1.04 ml (0.009 mol) of benzoyl chloride and boiled at reflux for 18 hrs. The reaction mixture was concentrated and the residue was chromatographed over silica gel with ethyl acetate/hexane (1:3). 0.415 g (44%) of 1-(4-fluoro-benzyl)-piperidin-4-yl benzoate was obtained as a yellow oil. MS: me/e=314 (C19H21FNO2+).

Workup

  1. temperatureat reflux for 18 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was chromatographed over silica gel with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-ed7864c851374026a71d3da3366db1e8
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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