Cyclohexylamine hydrochloride → Adamantan-1-yl-N'-cyclohexylguanidine HCl

HRID 1441169

Reaktionsgleichung

Reaktionsgleichung von HRID 1441169
[C:1]12([NH:11][C:12]#[N:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[ClH:14].[CH:15]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[ClH:14].[C:1]12([NH:11][C:12]([NH:21][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[NH:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Komponenten

3

Edukt 2

HCID 2723770Cyclohexylamine hydrochlorideHCID 124358461-Adamantylcyanamide

Produkt 1

HCID 178479309Adamantan-1-yl-N'-cyclohexylguanidine HCl

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

Adamantan-1-ylcyanamide (514 mg, 2.92 mmol), and cyclohexylamine hydrochloride (398 mg, 2.93 mmol) were finely ground together, and heated at 200° C. for 10 min. The resultant glassy solid was pulverized, and extracted twice with 50 ml boiling 5% HCl. The insoluble material was filtered, and dried. 346 mg, mp 264°-270° (p.h.b. 240° C.). On cooling the combined aqueous extracts to 25°, a white ppt. formed, and was filtered off, 56 mg. Combined crude yield: 44%. Crystallization of a 50 mg sample of the crude product from EtOH/Et2O afforded white needles (25 mg, mp 269°-271° C. (p.h.b. 240°), lit. 268°-269° C.). 1H (CD3OD) 1.208-1.474 (m, 5H), 1.744 (s, 9H), 1.967 (s, H), 2.119 (5, 3H), 3.434 (m, 1H), 13C (CD3OD) (broad band decoupled) 5.55, 26.26, 30.96, 33.74, 36.74, 42.73.

Aufarbeitung

  1. extractionextracted twice with 50 ml
  2. filtrationThe insoluble material was filtered
  3. customdried
  4. custom346 mg, mp 264°-270° (p.h.b. 240° C.)
  5. temperatureOn cooling the combined aqueous extracts to 25°
  6. customformed
  7. filtrationwas filtered off
  8. customCrystallization of a 50 mg sample of the crude product from EtOH/Et2O afforded white needles (25 mg, mp 269°-271° C. (p.h.b. 240°), lit. 268°-269° C.)

Quellen und Nachweise

ORD-Eintrag
ord-4bfd28d985094bdba3f2597658bb8757
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05502255

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