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

HRID 1033788

Reaction equation

[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

Participants

Reactant 2

HCID 2723770Cyclohexylamine hydrochloride

HCID 124358461-Adamantylcyanamide

Product 1

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

Conditions

Temperature: 200 °C

Procedure

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, 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.

Workup

extractionextracted twice with 50 ml
filtrationThe insoluble material was filtered
customdried
custom346 mg, mp 264-270 (p.h.b. 240° C.)
temperatureOn cooling the combined aqueous extracts to 25°
customformed
filtrationwas filtered off
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.)

Sources & evidence

ORD record: ord-11dbdf82c8df4c8ab19eb5b3d1e28d7e
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05312840

Linked notes

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