Triethylamine → 1-[beta-(2-Methyl-3-indolyl)propionyl]-4-benzyl-4-hydroxypiperidine

HRID 26174

Reaktionsgleichung

Reaktionsgleichung von HRID 26174
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.C(N(CC)CC)C.ClC(OCC)=O.[CH2:29]([C:36]1([OH:42])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][C:13]([N:39]1[CH2:38][CH2:37][C:36]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([OH:42])[CH2:41][CH2:40]1)=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 973801H-Indole-3-propanoic acid, 2-methyl-HCID 981524-Benzyl-4-piperidinol

Produkt 1

HCID 213246711-[beta-(2-Methyl-3-indolyl)propionyl]-4-benzyl-4-hydroxypiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred solution of 5.0 g of β-(2-methyl-3-indolyl)propionic acid and 2.5 g of triethylamine in 100 ml of chloroform was added dropwise 2.7 g of ethyl chloroformate at a temperature below 0° C. After the addition was complete, stirring was continued for additional 15 minutes and thereto was added 4.7 g of 4-benzyl-4-hydroxypiperidine in several portions. The reaction mixture was stirred for 4 hours at room temperature and allowed to stand overnight. The reaction product was washed thoroughly with water and concentrated to dryness. The residue was recrystallized from ethanol to give 1-[β-(2-methyl-3-indolyl)propionyl]-4-benzyl-4-hydroxypiperidine, melting at 117°-119° C.

Aufarbeitung

  1. additionAfter the addition
  2. stirringThe reaction mixture was stirred for 4 hours at room temperature
  3. waitto stand overnight
  4. washThe reaction product was washed thoroughly with water
  5. concentrationconcentrated to dryness
  6. customThe residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-3024e340990f494fa08720f195cbe64d
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04148796

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