Triethylamine → HCID 18919740, compound

HRID 1291180Notes

Reaction equation

HRID 1291180 reaction equation
[Cl: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.[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([O:13][CH:10]2[CH2:9][CH2:8][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:15][CH:14]=3)[CH2:12][CH2:11]2)=[O:29])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 764482HCID 764482, compound

Product 1

HCID 18919740HCID 18919740, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.226 g (0.001 mol) of 1-(4-chloro-benzyl)-piperidin-4-ol and 0.350 ml (0.0025 mol) of triethylamine were dissolved in 10 ml of toluene, treated with 0.16 ml (0.00125 mol) of 4-chloro-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 (1:3). 0.28 g (77%) of 1-(4-chloro-benzyl)-piperidin-4-yl 4-chloro-benzoate was obtained as colorless crystals; m.p. 67°-69°.

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-85c535e0ff0f46119a96e9636241da01
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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