Dicyclohexylamine → Dicyclohexylammonium chloride

HRID 1683803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683803
N1CCC(C2N=CNC=2)CC1.[CH:12]1([NH:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C1(CCCCC([Cl:37])=O)CCCCC1>C(#N)C.ClCCl>[Cl-:37].[CH:19]1([NH2+:18][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Komponenten

6

Edukt 3

HCID 7582DicyclohexylamineHCID 152333055-Cyclohexylpentanoyl chlorideHCID 1784208734-(1H-imidazol-4-yl)piperidine

Produkt 1

HCID 69082364Dicyclohexylammonium chlorideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 755 mg (5.00 mmol) 4-(4-piperidyl) 1-H-imidazole and 942 mg (5.20 mmol) of dicyclohexylamine in 10 ml anhydrous acetonitrile at 25° C. was slowly added 1.06 g (5.20 mmol) cyclohexanevaleroyl chloride in 2 ml of dichloromethane over a period of 10 min with stirring; then the reaction mixture was heated at 60° C. for 1.5 h. After cooling to ambient temperature, the solid side product that was obtained (dicyclohexylammonium chloride) was filtered off and the filtrate was concentrated in vacuo to remove acetonitrile. The resulting crude oil was crystallized with methanol: anhydrous diethyl ether to give 1.085 mg of analytically pure product as a yellow powder. Yield: 68%; M.P.: 159° C.; MS: m/e=317(M+); 1H NMR (CDCl3): imidazole H: δ 7.65 (s, 1H), 6.75 (s, 1H); cyclohexylbutyl: δ 2.20 (m, 8H), 1.20 (m, 11H); piperidyl: 4.65 (d, 2H), 3.95 (d, 2H), 3.10 (d, 2H), 2.84 (m, 1H), 2.20 (m, 2H).

Aufarbeitung

  1. customof 10 min
  2. temperatureAfter cooling to ambient temperature

Quellen und Nachweise

ORD-Eintrag
ord-dc37e313768e4be387f446e4f3738a87
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639775

Notizen zur Reaktion

Wird geladen…