Cyanamide → HCID 66779286, compound

HRID 406332Notes

Reaction equation

HRID 406332 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])[C:3]1=O.[N:20]#[C:21][NH2:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(O)C.C(OCC)(=O)C.C(N(CC)CC)C>[F:16][C:15]([F:18])([F:17])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][CH:4]1[CH2:5][CH2:6][CH2:7][N:2]2[N:1]=[C:21]([NH2:22])[N:20]=[C:3]12

Participants

8

Reactant 4

HCID 9864CyanamideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 66633947HCID 66633947, compound

Product 1

HCID 66779286HCID 66779286, compoundYield 24.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1-Amino-3-(2-trifluoromethylbenzyl)piperidin-2-one (916 mg) and cyanamide (849 mg) were dissolved in ethanol (15 mL). p-Toluenesulfonic acid monohydrate (961 mg) was added and the mixture was heated under reflux at 80° C. for 3.5 hours. After cooling to room temperature, triethylamine (2.3 mL) was added and the mixture was further heated under reflux at 80° C. for four days. A sodium bicarbonate solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the organic layer was concentrated under reduced pressure. The resulting solid was washed with ethyl acetate to obtain the title compound (244 mg). The property values of the compound are as follows.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling to room temperature
  3. temperaturethe mixture was further heated
  4. temperatureunder reflux at 80° C. for four days
  5. customthe organic layer was separated
  6. washThe resulting organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe drying agent was separated by filtration
  9. concentrationthe organic layer was concentrated under reduced pressure
  10. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-6f4bb71ed63740308333d06bf8bcd7c6
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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