Triethylamine → HCID 18919876, compound

HRID 1291096Notes

Reaction equation

HRID 1291096 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.[C:22]1([CH3:31])[CH:27]=[CH:26][CH:25]=[C:24]([C:28](Cl)=[O:29])[CH:23]=1>C1(C)C=CC=CC=1>[CH3:31][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=1)[C:28]([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:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743753-Methylbenzoyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 18919876HCID 18919876, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.0 g (0.00532 mol) of 1-benzyl-4-hydroxypiperidine and 0.72 ml (0.00532 mol) of triethylamine were dissolved in 50 ml of toluene and treated with 0.7 ml (0.00532 mol) of m-toluoyl 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). 1.07 g (65%) of 1-benzyl-piperidin-4-yl 3-methyl-benzoate were obtained as a yellow solid: m.p. 45°-46°.

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)

Sources & evidence

ORD record
ord-4fe6dd845e9a448a9f190ff5f40caf11
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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