Benzoyl chloride → HCID 18919768, compound

HRID 1291133Notes

Reaction equation

HRID 1291133 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.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]([Br: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 677772HCID 677772, compound

Product 1

HCID 18919768HCID 18919768, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.108 g (0.0004 mol) of 1-(4-bromo-benzyl)-piperidin-4-ol and 0.12 ml (0.00085 mol) of triethylamine were dissolved in 4 ml of toluene, treated with 0.058 ml (0.0005 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 (1:1). 0.125 g (83.5%) of 1-(4-bromo-benzyl)-piperidin-4-yl benzoate was obtained as a colorless oil.

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 (1:1)

Sources & evidence

ORD record
ord-55c4a3f9062742f09cfb731f1225357c
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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