Cyclohexylamine → HCID 68553017, compound

HRID 2036092Notes

Reaction equation

HRID 2036092 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:5][CH2:4]2)[CH2:2]1.[CH:19]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[CH:19]1([NH:25][CH2:2][C:3]2([OH:1])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:5][CH2:4]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 13016598Benzyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylateHCID 23665649Lithium perchlorate

Product 1

HCID 68553017HCID 68553017, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (1.98 g) was dissolved in acetonitrile (80 mL), and cyclohexylamine (800 mg) and lithium perchlorate (960 mg) were added. The mixture was stirred at 80° C. overnight, and cooled to room temperature. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography using basic silica gel (15% ethyl acetate/hexane to 80% ethyl acetate/hexane) to give the object product (2.39 g, 96%).

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-daf59e2da2494f2cb104f0a3adb4728d
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

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