Triethylamine → HCID 18919761, compound

HRID 1291174Notes

Reaction equation

HRID 1291174 reaction equation
[CH3:1][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]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:13][CH:10]2[CH2:9][CH2:8][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:15][CH:14]=3)[CH2:12][CH2:11]2)=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 7914821-(4-Methylbenzyl)piperidin-4-ol

Product 1

HCID 18919761HCID 18919761, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.31 g (0.0015 mol) of 1-(4-methyl-benzyl)-piperidin-4-ol and 0.52 ml (0.00375 mol) of triethylamine were dissolved in 15 ml of toluene, treated with 0.25 ml (0.001875 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 (1:4). 0.4 g (83%) of 1-(4-methyl-benzyl)-piperidin-4-yl 4-methyl-benzoate was obtained as yellow crystals; m.p. 66°-77°.

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 (1:4)

Sources & evidence

ORD record
ord-8b661b99a648451d97b3e487f747a4bb
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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