Triethylamine → 1-Benzyl-piperidin-4-yl 2-methoxy-benzoate

HRID 1291099

Reaction equation

HRID 1291099 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:22][O:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>C1(C)C=CC=CC=1>[CH3:22][O:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([O:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1)=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 784611-Benzylpiperidin-4-olHCID 889692-Methoxybenzoyl chloride

Product 1

HCID 189197861-Benzyl-piperidin-4-yl 2-methoxy-benzoateYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.41 g (0.00733 mol) of 1-benzyl-4-hydroxypiperidine and 1.8 ml (0.0129 mol) of triethylamine were dissolved in 50 ml of toluene and treated with 0.79 ml (0.00586 mol) of 2-methoxy-benzoyl chloride. The mixture was boiled at reflux for 2 hrs., the precipitate was filtered off and the filtrate was concentrated. The residue was chromatographed over silica gel with ethyl acetate/hexane (1:2). 1.31 g (69%) of 1-benzyl-piperidin-4-yl 2-methoxy-benzoate were obtained as a yellowish oil. MS: me/e=326 (C20H24NO3 +).

Workup

  1. temperatureat reflux for 2 hrs
  2. filtration, the precipitate was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was chromatographed over silica gel with ethyl acetate/hexane (1:2)

Sources & evidence

ORD record
ord-0cd03ccf5b6c4bdf9ce9ae0f7e0f9d26
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Linked notes

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