HCID 21922938, compound → HCID 178478726, compound

HRID 1272663Notes

Reaction equation

HRID 1272663 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][CH2:21][CH2:20]2)=[C:12]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH:26]=2)[N:11]=1>O>[ClH:9].[ClH:9].[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)=[C:12]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:27][CH:26]=3)[N:11]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21922938HCID 21922938, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178478726HCID 178478726, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

342 mg of trans-1,4-diaminocyclohexane is taken to approximately 150° C. then 234 mg of the product obtained in Stage 1 above is added, the reaction medium is maintained under agitation at 140° C. for 9 hours 30 minutes then left to return to ambient temperature. Then 10 ml of water is added, followed by extracting with dichloromethane, drying and evaporating the solvent. The residue is chromatographed on silica (eluent: MeOH/NH4OH 98/2), followed by taking up in 5 ml of an ethanolic solution of hydrochloric acid, evaporating the solvents, impasting the residue in ether and drying under reduced pressure at 60° C. 93 mg of expected product is recovered.

Workup

  1. customis taken to approximately 150° C.
  2. waitthen left
  3. customto return to ambient temperature
  4. extractionby extracting with dichloromethane
  5. customdrying
  6. customevaporating the solvent
  7. customThe residue is chromatographed on silica (eluent: MeOH/NH4OH 98/2)
  8. customevaporating the solvents
  9. customdrying under reduced pressure at 60° C
  10. custom93 mg of expected product is recovered

Sources & evidence

ORD record
ord-8bd9d79d071d4e7e991e5e88c63ee5fa
Source dataset
uspto-grants-2007_04
Patent number
US07208598B2

Reaction notes

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