Triethylamine → HCID 18919788, compound

HRID 1291095Notes

Reaction equation

HRID 1291095 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.[I: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>[I: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 743734-Iodobenzoyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 18919788HCID 18919788, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.75 g (0.00394 mol) of 1-benzyl-4-hydroxy-piperidine and 0.546 ml (0.00394 mol) of triethylamine were dissolved in 50 ml of toluene and treated with 1.0 g (0.00375 mol) of 4-iodobenzoyl 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). 1.07 g (68%) of 1-benzyl-piperidin-4-yl 4-iodo-benzoate were obtained as yellow crystals; m.p. 77°-78°.

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-bb8a23c81de14d14ae4edff853b1f60b
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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