Triethylamine → HCID 18919750, compound

HRID 1291138Notes

Reaction equation

HRID 1291138 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]1([CH3:32])[CH:28]=[CH:27][C:26]([C:29](Cl)=[O:30])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[CH3:32][C:23]1[CH:28]=[CH:27][C:26]([C:29]([O:11][CH:8]2[CH2:9][CH2:10][N:5]([CH2:4][C:3]3[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=3[Cl:1])[CH2:6][CH2:7]2)=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 18919865HCID 18919865, compound

Product 1

HCID 18919750HCID 18919750, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.451 g (0.002 mol) of 1-(2-chloro-benzyl)-piperidin-4-ol and 1.23 ml (0.0088 mol) of triethylamine were dissolved in 4 ml of toluene, treated with 0.331 ml (0.0025 mol) of p-toluoyl 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). 0.3 g (44%) of 1-(2-chloro-benzyl)-piperidin-4-yl 4-methyl-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-2f1a08fd8b334a70975fb28dd5eb0025
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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