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Triethylamine → 4-Methanesulphonamido-1-(4-phenyl-4-oxobutyl)piperidine

HRID 258713
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 258713
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:12])[CH2:4][CH2:3]1)(=[O:29])=[O:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 126085374-Amino-1-(4-phenyl-4-oxobutyl)piperidine

Produkt 1

HCID 214265254-Methanesulphonamido-1-(4-phenyl-4-oxobutyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-Amino-1-(4-phenyl-4-oxobutyl)piperidine (1.23 g. 0.005 m) was suspended in a solution of dichloromethane (10 mls) containing triethylamine (2 mls). Methanesulphonyl chloride (0.570 g, 0.005 m) in dichloromethane (5 mls) was added dropwise over 5 minutes and the reaction stirred overnight at room temperature. The solution was then washed with five aliquots of water and dried over magnesium sulphate. Evaporation yielded the free base in 90% purity. This was triturated in ethyl acetate and warmed. The mother liquor was decanted off and evaporated to yield the title compound m.pt 141.4° C. This was recrystallised from ethanolic HCl as the hydrochloride salt (0.510 g), m.pt 167.4° C.

Aufarbeitung

  1. washThe solution was then washed with five aliquots of water
  2. dry with materialdried over magnesium sulphate
  3. customEvaporation
  4. customyielded the free base in 90% purity
  5. customThis was triturated in ethyl acetate
  6. temperaturewarmed
  7. customThe mother liquor was decanted off
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-516f769c74dc4c6db94b5b6c9bfb32dc
Quelldatensatz
uspto-grants-1977_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04034098

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