Water → HCID 178479703, compound

HRID 1244951Notes

Reaction equation

HRID 1244951 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][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[OH2:23]>C(OCC)(=O)C>[ClH:1].[CH:11]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([NH:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]2)=[N:3][C:4]=3[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 962WaterHCID 21922983HCID 21922983, compound

Product 1

HCID 178479703HCID 178479703, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

575 mg of trans-1,4-aminocyclohexanol are mixed together and the reaction medium is taken to a temperature of 50 to 60° C. then 313 mg of the product obtained in Stage 1 above is added and agitation is carried out at a temperature of 150 to 160° C. for approximately 20 hours. The reaction medium is then left to return to ambient temperature, taken up in ethyl acetate and water and then taken to a temperature of approximately 60° C. and left to settle, followed by re-extracting with ethyl acetate, washing with a saturated aqueous solution of sodium chloride, drying and evaporating to dryness. The residue is chromatographed on silica (eluent: CH2Cl2/MeOH 95/5), taken up in an ethanolic solution of hydrochloric acid and left to crystallize, followed by separating, drying under reduced pressure and 266 mg of expected product is recovered.

Workup

  1. customis taken to a temperature of 50 to 60° C.
  2. waitThe reaction medium is then left
  3. customto return to ambient temperature
  4. customtaken to a temperature of approximately 60° C.
  5. waitleft
  6. extractionby re-extracting with ethyl acetate
  7. washwashing with a saturated aqueous solution of sodium chloride
  8. customdrying
  9. customevaporating to dryness
  10. customThe residue is chromatographed on silica (eluent: CH2Cl2/MeOH 95/5)
  11. waitleft
  12. customto crystallize
  13. customby separating
  14. dry with materialdrying under reduced pressure and 266 mg of expected product
  15. customis recovered

Sources & evidence

ORD record
ord-a8e11eadb5094ccfa62ccf19673b7c21
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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