Ethyl Acetate → HCID 18457591, compound

HRID 1272617Notes

Reaction equation

HRID 1272617 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH2:8])[CH2:4][CH2:3]1.[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[CH:19]2[CH2:23][CH2:22][O:21][CH2:20]2)=[C:12]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:11]=1.C(OCC)(=O)C>O>[ClH:9].[ClH:9].[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH:19]3[CH2:23][CH2:22][O:21][CH2:20]3)=[C:12]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:11]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21923050HCID 21923050, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 18457591HCID 18457591, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

656 mg of trans-1,4-diaminocyclohexane and 133 mg of the product obtained in Stage 2 above are mixed together and the reaction medium is taken to a temperature of 130 to 150° C. for approximately 5 hours then left overnight at ambient temperature. Then the reaction medium is taken up in 10 ml of water and 20 ml of ethyl acetate and left to settle, followed by re-extracting with 2×5 ml of ethyl acetate, washing with 10 ml of water and 10 ml of saturated aqueous solution of sodium chloride, drying and evaporating to dryness. After purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2, 1.5 ml of hydrochloric acid at 1.4 N in ethanol is added and the reaction medium is left to crystallize. After diluting with 2 ml of ethyl acetate and leaving for one hour at ambient temperature, separation is carried out, followed by washing with 5 ml of ethyl acetate and drying at a temperature of approximately 50° C. In this way 98 mg of expected product is obtained in the form of white/cream crystals.

Workup

  1. waitthen left overnight at ambient temperature
  2. extractionby re-extracting with 2×5 ml of ethyl acetate
  3. washwashing with 10 ml of water and 10 ml of saturated aqueous solution of sodium chloride
  4. customdrying
  5. customevaporating to dryness
  6. customAfter purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2, 1.5 ml of hydrochloric acid at 1.4 N in ethanol
  7. additionis added
  8. waitthe reaction medium is left
  9. customto crystallize
  10. additionAfter diluting with 2 ml of ethyl acetate
  11. customleaving for one hour at ambient temperature
  12. customseparation
  13. washby washing with 5 ml of ethyl acetate
  14. customdrying at a temperature of approximately 50° C

Sources & evidence

ORD record
ord-103fc3c717ab4e06a2bf6c5ff4e4afcf
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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