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

HRID 1900142

反応式

HRID 1900142 の反応式
[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

参加物

3

反応物 2

HCID 2723770Cyclohexylamine hydrochlorideHCID 124358461-Adamantylcyanamide

生成物 1

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

反応条件

温度
200 °C

実験手順

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.

後処理

  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.)

出典と根拠

ORDレコード
ord-486906e6b7c4482b9674b7d3edc1185a
出典データセット
uspto-grants-1996_11
特許番号
US05574070

関連ノート

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