Dicyclohexylamine → Dicyclohexylammonium chloride

HRID 375580Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 755 mg (5.00 mmol) 4-(4-piperidyl)1-H-imidazole and 942 mg (5.20 mmol) of ##STR7## 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, 1 H), 6.75 (s, 1 H); cyclohexylbutyl: δ 2.20 (m, 8 H), 1.20 (m, 11 H); piperidyl: 4.65 (d, 2 H), 3.95 (d, 2 H), 3.10 (d, 2 H), 2.84 (m, 1 H), 2.20 (m, 2 H).

Workup

customof 10 min
temperatureAfter cooling to ambient temperature

Sources & evidence

ORD record: ord-8e084594376644198e40fb866ef0df30
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486526

Reaction notes

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