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

HRID 1900142

반응식

HRID 1900142 반응식
[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

참가 물질

3

반응물 2

HCID 2723770Cyclohexylamine hydrochlorideHCID 124358461-Adamantylcyanamide

생성물 1

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

반응 조건

온도
200 °C

실험 절차

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) δ1.208-1.474 (m, 5H), 1.744 (s, 9H), 1.967 (s, 8H), 2.119 (5, 3H), 3.434 (m, 1H), 13C (CD3OD) (broad band decoupled) 25.55, 26.26, 30.96, 33.74, 36.74, 42.73.

후처리

  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.)

출처 및 근거

ORD 기록
ord-486906e6b7c4482b9674b7d3edc1185a
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05574070

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