Triethylamine → HCID 18919832, compound

HRID 1291131Notes

Reaction equation

HRID 1291131 reaction equation
[Br: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]([Br: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 765218184921-06-0

Product 1

HCID 18919832HCID 18919832, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.38 g (0.001.41 mol) of 1-(3-bromo-benzyl)-piperidin-4-ol and 0.49 ml (0.0035 mol) of triethylamine were dissolved in 4 ml of toluene, treated with 0.23 ml (0.00176 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). 0.358 g (65%) of 1-(3-bromo-benzyl)-piperidin-4-yl 4-methyl-benzoate was obtained as a yellow 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 (1:4)

Sources & evidence

ORD record
ord-dd214c0bcc13437aac6b60cf691830cc
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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