Cyclohexylamine → HCID 44182393, compound

HRID 1436314Notes

Reaction equation

HRID 1436314 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:24])[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]4[CH2:23][O:22]4)=[CH:15][CH:14]=3)=[CH:9][O:10]2)=[CH:5][CH:4]=1.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C(O)C>[CH:25]1([NH:31][CH2:23][CH:21]([OH:22])[CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([C:8]3[C:7](=[O:24])[C:6]4[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[O:10][CH:9]=3)=[CH:14][CH:15]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 44227176HCID 44227176, compound

Product 1

HCID 44182393HCID 44182393, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 3 (obtained from example 1) (0.32 g, 1 mmol), cyclohexylamine (0.50 g, 5 mmol), and ethanol (30 mL) was refluxed for 4 hrs (TLC monitoring). After removal of solvent in vacuo, the residue was treated with H2O (50 mL). The resulting precipitate was collected and purified by column chromatography (MeOH/CH2Cl2=1:20) to give the title compound 5c (0.28 g, 67% yield). M.p.: 125-126° C.

Workup

  1. temperaturewas refluxed for 4 hrs (TLC monitoring)
  2. customAfter removal of solvent in vacuo
  3. additionthe residue was treated with H2O (50 mL)
  4. customThe resulting precipitate was collected
  5. custompurified by column chromatography (MeOH/CH2Cl2=1:20)

Sources & evidence

ORD record
ord-28ccf6a604ce436faddab2871c052667
Source dataset
uspto-grants-2009_11
Patent number
US07618998B2

Reaction notes

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