Hydrochloric Acid → HCID 66778849, compound

HRID 2094200Notes

Reaction equation

HRID 2094200 reaction equation
[O-:1][C:2]#N.[K+].[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([NH:13][C:14]2([C:20]#[N:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:9][CH:8]=1.Cl.[OH2:23]>C(O)(=O)C>[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([N:13]2[C:14]3([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:20](=[O:23])[NH:21][C:2]2=[O:1])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 11378442Potassium cyanateHCID 66618552HCID 66618552, compound

Product 1

HCID 66778849HCID 66778849, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

2.8 g (34.5 mmol, 1.6 eq.) of potassium cyanate are added at 30° C. to a solution of 5 g (21.6 mmol, 1 eq.) of 1-(6-methoxypyridin-3-ylamino)-cyclohexanecarbonitrile in 50 ml of glacial acetic acid. The reaction medium is stirred at 60° C. for 4 hours. 8 ml of hydrochloric acid and then 5 ml of water are added. The medium is heated at 90° C. for 1 hour and then at room temperature for 24 hours. It is then poured into 30 ml of water. The aqueous phase is extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over sodium sulfate. The solvents are evaporated off. The residue is chromatographed on silica gel (90/10 dichloromethane/methanol). The product is precipitated from dichloromethane and heptane and then filtered off and dried. 1-(6-Methoxypyridin-3-yl)-1,3-diaza-spiro[4.5]decane-2,4-dione is obtained in the form of a white solid.

Workup

  1. temperatureThe medium is heated at 90° C. for 1 hour
  2. waitat room temperature for 24 hours
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialThey are dried over sodium sulfate
  6. customThe solvents are evaporated off
  7. customThe residue is chromatographed on silica gel (90/10 dichloromethane/methanol)
  8. customThe product is precipitated from dichloromethane and heptane
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-ef18790cef984fdfb52217cb8ad6acff
Source dataset
uspto-grants-2013_05
Patent number
US08445523B2

Reaction notes

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