Benzyl Alcohol → HCID 18919846, compound

HRID 1291189Notes

Reaction equation

HRID 1291189 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[CH2:6][CH2:7][CH:9]([C:8]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:15])[CH2:5][CH2:4]1)[C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 8471Triethylamine

Product 1

HCID 18919846HCID 18919846, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.278 g (0.00127 mol) of 1-benzylpiperidine-4-carboxylic acid was boiled at reflux in 5 ml of oxalyl chloride for 2 hrs. The excess oxalyl chloride was distilled off. The residue was taken up twice in toluene and concentrated each time. 0.3 g (99%) of 1-benzylpiperidine-4-carboxylic acid chloride was obtained as a pale beige solid. This was dissolved in 20 ml of toluene, treated with 0.265 ml (0.0019 mol) of triethylamine and 0.17 g (0.00165 mol) of benzyl alcohol and boiled at reflux for 18 hrs. After removal of the solvent the residue was chromatographed on silica gel with ether/hexane (1:2) as the eluent. 0.246 g (80%) of benzyl 1-benzylpiperidin-4-carboxylate was obtained as a yellow oil. MS: me/e=310 (C2H23NO2+).

Workup

  1. temperatureat reflux for 18 hrs
  2. customAfter removal of the solvent the residue
  3. customwas chromatographed on silica gel with ether/hexane (1:2) as the eluent

Sources & evidence

ORD record
ord-4949980c313f419f8f0ccfce250e001e
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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