Dicyclohexylamine → HCID 67197281, compound

A solution of dicyclohexylamine (4.0 mL, 20 mmol) and triethylamine (6 mL, 43 mmol) in diethyl ether (63 mL) was added dropwise to a stirred solution of triphosgene (2.0 g, 6.7 mmol) in diethyl ether (30 mL) at room temperature. The reaction mixture was stirred overnight under refluxing conditions. Then, a solution of piperidine (1.9 mL, 19 mmol) and triethylamine (5.8 mL, 42 mmol) in diethyl ether (37 mL) was added. The reaction mixture was stirred overnight at reflux temperature. The reaction mixture was filtered and the filtrate was evaporated to dryness, yielding N,N-dicyclohexylpiperidylurea as a yellow oil. Yield: 2.0 g (35%). Oxalyl chloride (1.0 mL, 12 mmol) was added to a stirred solution of the urea (2.0 g, 6.9 mmol) in diethyl ether (30 mL). The reaction mixture was evaporated to dryness after stirring at reflux temperature for 5 h. Ammonia (3 mL, 21 mmol, 7 M solution in methanol) was added to a solution of the resulting solid in diethyl ether (50 mL) and THF (5 mL). The reaction mixture was heated to reflux overnight and evaporated to dryness. The product mixture was treated with aqueous sodium hydroxide solution. The organic layer was extracted with diethyl ether and dried over sodium sulfate. Filtration and evaporation to dryness yielded the desired guanidine as a yellow solid. Yield: 1.76 g (87%). 1H NMR (CDCl3, 300 MHz): δ 1.18-1.89 (m 20 H), 3.03 (m, 6 H) ppm. 13C NMR (CDCl3, 75 MHz): δ 25.2, 26.1, 26.2, 32.4, 49.0, 57.8, 165.2 ppm.

1. stirringThe reaction mixture was stirred overnight
2. temperatureat reflux temperature
3. filtrationThe reaction mixture was filtered
4. customthe filtrate was evaporated to dryness

ORD record

ord-490baaae51514d56b088c9ad99ae1b62

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987393B2