Benzoyl chloride → HCID 18919805, compound

HRID 1291136Notes

Reaction equation

HRID 1291136 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]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:11][CH:8]1[CH2:9][CH2:10][N:5]([CH2:4][C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=2[Cl:1])[CH2:6][CH2:7]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 18919865HCID 18919865, compound

Product 1

HCID 18919805HCID 18919805, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.14 g (0.00062 mol) of 1-(2-chloro-benzyl)-piperidin-4-ol and 0.17 ml (0.00123 mol) of triethylamine were dissolved in 6.2 ml of toluene, treated with 0.09 ml (0.000776 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→1:2). 0.16 g (78%) of 1-(2-chloro-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→1:2)

Sources & evidence

ORD record
ord-8b1cf844f1cd48049a1a726dc60491df
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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