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

HRID 1291081Notes

Reaction equation

HRID 1291081 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.[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>C1(C)C=CC=CC=1>[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([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:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 189197891-Benzyl-piperidin-4-yl 2-chloro-benzoateYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.2 g (0.00105 mol) of 1-benzyl-4-hydroxypiperidine and 0.26 ml (0.00184 mol) of triethylamine were dissolved in 10 ml of toluene and treated with 0.11 ml (0.00084 mol) of 2-chloro-benzoyl chloride. The mixture was boiled at reflux for 6 hrs., the precipitate was filtered off and the filtrate was concentrated. The residue was chromatographed over silica gel with ethyl acetate/hexane (1:2). 0.262 g (95%) of 1-benzyl-piperidin-4-yl 2-chloro-benzoate was obtained as white crystals; m.p. 143°-144°.

Workup

  1. temperatureat reflux for 6 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-8218242d090e47f9abb8cbe7a7f52b7c
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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