Triethylamine → 1-Benzyl-piperidin-4-yl 3-methoxy-benzoate

HRID 1291100Notes

Reaction equation

HRID 1291100 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:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28]>C1(C)C=CC=CC=1>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([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:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 189198061-Benzyl-piperidin-4-yl 3-methoxy-benzoateYield 80%

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 3-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 (1:3→1:2→1:1)). 1.52 g (80%) of 1-benzyl-piperidin-4-yl 3-methoxy-benzoate were obtained as a yellowish oil. MS: me/e (% basic peak)=325 (C20H23NO3+, 7.6), 248 (4), 173 (30.3), 135 (13), 91 (78), 82 (100).

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 (1:3→1:2→1:1))

Sources & evidence

ORD record
ord-8e4404bb30004402a5a4daf3702dad87
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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