Triethylamine → 1-Benzyl-piperidin-4-yl 3-iodo-benzoate

HRID 1291094

Reaktionsgleichung

Reaktionsgleichung von HRID 1291094
[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:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>C1(C)C=CC=CC=1>[I:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([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:27]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 743783-Iodobenzoyl chlorideHCID 784611-Benzylpiperidin-4-ol

Produkt 1

HCID 189198621-Benzyl-piperidin-4-yl 3-iodo-benzoateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

1.21 g (0.0063 mol) of 1-benzyl-4-hydroxypiperidine and 0.874 ml (0.0063 mol) of triethylamine were dissolved in 80 ml of toluene and treated with 1.6 g (0.006 mol) of 3-iodo-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). 1.9 g (76%) of 1-benzyl-piperidin-4-yl 3-iodo-benzoate were obtained as yellowish crystals; m.p. 101°-103°.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a9a5a14b86064033b64ff2fb81d7da3c
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753679

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