Benzoyl chloride → HCID 15124790, compound

HRID 1291074Notes

Reaction equation

HRID 1291074 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](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[C:22]([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])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 15124790HCID 15124790, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.5 g (0.00216 mol) of 1-benzyl-4-hydroxypiperidine and 0.64 ml (0.0046 mol) of triethylamine were dissolved in 20 ml of toluene, treated with 0.313 ml (0.0027 mol) of benzoyl chloride and boiled at reflux for 6 hrs. The suspension was filtered, the filtrate was concentrated and the residue was chromatographed over silica gel with ethyl acetate/hexane (1:3) as the eluent. 0.525 g (82%) of 1-benzyl-piperidin-4-yl benzoate was obtained as yellowish oil.

Workup

  1. temperatureat reflux for 6 hrs
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated
  4. customthe residue was chromatographed over silica gel with ethyl acetate/hexane (1:3) as the eluent

Sources & evidence

ORD record
ord-656ce1503efc4e2b9b53662e61594ce1
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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