Triethylamine → HCID 18919848, compound

HRID 1291085Notes

Reaction equation

HRID 1291085 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][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([O:14][CH:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH2:10]2)=[O:28])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 18919848HCID 18919848, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.3 g (0.0015 mol) of 1-benzyl-4-hydroxypiperidine and 0.216 ml (0.00155 mol) of triethylamine were dissolved in 20 ml of toluene and treated with 0.21 ml (0.0016 mol) of 4-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). 0.404 g (82%) of 1-benzyl-piperidin-4-yl 4-chloro-benzoate was obtained as a colorless oil. MS: me/e (% basic peak)=329 (C19H20CINO2+, 7), 252 (7), 173 (32), 139 (15), 91 (91), 82 (100).

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-1659c93d1e12448ea32d84fcccc09c1d
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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