Triethylamine → HCID 18919901, compound

HRID 1291142Notes

Reaction equation

HRID 1291142 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]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:12][CH:9]2[CH2:8][CH2:7][N:6]([CH2:5][C:4]3[CH:13]=[CH:14][CH:15]=[C:2]([Cl:1])[CH:3]=3)[CH2:11][CH2:10]2)=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 6456163HCID 6456163, compound

Product 1

HCID 18919901HCID 18919901, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.25 g (0.0011 mol) of 1-(3-chloro-benzyl)-piperidin-4-ol and 0.39 ml (0.0028 mol) of triethylamine were dissolved in 11 ml of toluene, treated with 0.184 ml (0.0014 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 (1:3). 0.155 g (41%) of 1-(3-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 (1:3)

Sources & evidence

ORD record
ord-9f1d2473d5354d00a55d31e0cb9ad115
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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