Piperidine → HCID 853659, compound

HRID 540971Notes

Reaction equation

HRID 540971 reaction equation
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CCCCCC>[CH:1]1([NH:7][C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 18502Cyclohexyl isocyanate

Product 1

HCID 853659HCID 853659, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

23.8 g of cyclohexyl isocyanate (0.190 mol) are added dropwise to a solution of 18.62 g of piperidine (0.219 mol) in 360 ml of hexane, and then the cloudy mixture is refluxed for 2 h and then cooled and filtered, to give 39.3 g of pure N-cyclohexylpiperidine-1-carboxamide (yield 98.3%). 12 g of POCl3 (78 mmol) are added, over 1 h, to a suspension of 15.05 g of said N-cyclohexylpiperidine-1-carboxamide (71.6 mmol) in 65 ml of dry toluene, and then, after a few hours at 20° C., 18.1 g of N-butyl-N-ethylamine (0.179 mmol) are added over 2 h, and then, after a further 2 h at 20° C., 50 ml of water are added. 49 g of 35% sodium hydroxide are then added while cooling, and the two-phase medium is then extracted with diisopropyl ether. After drying and evaporation to dryness, the oil obtained, 20 g, is distilled at 185° C. under 1 mbar, to give 17 g of the expected guanidine (yield 81%).

Workup

  1. temperaturethe cloudy mixture is refluxed for 2 h
  2. temperaturecooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d148e3ed259640c49f0f6c2376ef7dcb
Source dataset
uspto-grants-2014_10
Patent number
US08871889B2

Reaction notes

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