Piperidine → HCID 853659, compound

HRID 1894910Notes

Reaction equation

HRID 1894910 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:7]1([N:13]=[C:14]=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>CCCCCC>[CH:7]1([NH:13][C:14]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 18502Cyclohexyl isocyanate

Product 1

HCID 853659HCID 853659, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 18.62 g of piperidine (0.219 mol) in 360 ml of hexane is admixed dropwise with 23.8 g of cyclohexyl isocyanate (0.190 mol) and then the cloudy mixture is heated at reflux for 2 hours, then cooled and filtered to give 39.3 g of pure N-cyclohexyl-piperidine-1-carboxamide (98.3% yield). A suspension of 15.05 g of this pure product (71.6 mmol) in 65 ml of dry toluene is admixed with 12 g of POCl3 (78 mmol) over 1 hour, and then, after a number of hours at 20° C., 18.1 g of N-butyl-N-ethylamine (0.179 mmol) are added over 2 hours, and then, after a further 2 hours at 20° C., 50 ml of water are added. 49 g of 35% sodium hydroxide solution are then added while cooling, after which the two-phase mixture is extracted with diisopropyl ether. Following 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 (81% yield).

Workup

  1. temperaturethe cloudy mixture is heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-da52471c7d83498a83fbd0c28f9eb276
Source dataset
uspto-grants-2013_08
Patent number
US08513370B2

Reaction notes

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