Ethyl Acetate → HCID 178479704, compound

HRID 1272619Notes

Reaction equation

HRID 1272619 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:3]=1.C([O:27][CH2:28][CH3:29])(=O)C>O>[ClH:1].[CH:11]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([NH:8][C@H:11]2[CH2:15][CH2:29][C@H:28]([OH:27])[CH2:13][CH2:12]2)=[N:3][C:4]=3[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 21923049HCID 21923049, compound

Product 1

HCID 178479704HCID 178479704, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

1 g of trans-1,4-aminocyclohexanol is mixed which is then taken to a temperature of 50 to 60° C. and 212 mg of the product obtained in Stage 1 above is added and taken to a temperature of 140 to 150° C. for approximately 4 hours. The reaction medium is then left to return to a temperature of 100° C., 10 ml of water is added, the reaction medium is left to settle, 10 ml of water, 20 ml of ethyl acetate are added and the medium is taken to a temperature of approximately 70° C. Then 10 ml of water is added and the reaction medium is left overnight at ambient temperature, then left to settle, followed by re-extracting with 2×20 ml of methylene chloride with 20% of methanol, combining the organic phases, washing with 10 ml of water and 10 ml of an aqueous solution of sodium chloride, drying and evaporating to dryness. The residue is then dissolved in the minimum amount of ethanol, 1.4N hydrochloric acid in ethanol is added and the reaction medium is left to crystallize, followed by diluting in 5 ml of ethanol then leaving for one hour at ambient temperature, separating, washing with 10 ml of ethanol and drying at a temperature of approximately 50° C. In this way 215 mg of expected product is obtained in the form of white crystals.

Workup

  1. additionabove is added
  2. waitThe reaction medium is then left
  3. additionis added
  4. waitthe reaction medium is left
  5. customis taken to a temperature of approximately 70° C
  6. waitthe reaction medium is left overnight at ambient temperature
  7. waitleft
  8. extractionby re-extracting with 2×20 ml of methylene chloride with 20% of methanol
  9. washwashing with 10 ml of water and 10 ml of an aqueous solution of sodium chloride
  10. customdrying
  11. customevaporating to dryness
  12. dissolutionThe residue is then dissolved in the minimum amount of ethanol, 1.4N hydrochloric acid in ethanol
  13. additionis added
  14. waitthe reaction medium is left
  15. customto crystallize
  16. additionby diluting in 5 ml of ethanol
  17. customthen leaving for one hour at ambient temperature
  18. customseparating
  19. washwashing with 10 ml of ethanol
  20. customdrying at a temperature of approximately 50° C

Sources & evidence

ORD record
ord-a5fdfbf2871b4d858c41420cfdb3bef3
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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