Ethanol → HCID 18441772, compound

HRID 458155

Reaction equation

HRID 458155 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[N:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(N(CC)CC)C.C([OH:41])C>>[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][N:16]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][C:26]3=[O:41])[CH2:15][CH2:14]2)[N:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 10952ChlorocyclohexaneHCID 184417443-Benzyl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

Product 1

HCID 18441772HCID 18441772, compound

Procedure

A solution of 0.30 g (0.93 mmol) 3-benzyl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one, 0.14 g (1.0 mmol) 2-chlorocyclohexane, and 0.2 ml (1.4 mmol) triethylamine in ethanol was refluxed overnight. The reaction mixture was cooled to ambient temperature, concentrated and then quenched with saturated NaHCO3 and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated. Purification of the crude product over a silica gel plug (10:1) with n-heptane/AcOEt as eluent provided 0.14 g rac-3-benzyl-8-(2-oxo-cyclohexyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one as a light yellow oil; MS (ISP): 418.4 MH+.

Workup

  1. concentrationconcentrated
  2. customquenched with saturated NaHCO3
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the crude product over a silica gel plug (10:1) with n-heptane/AcOEt as eluent

Sources & evidence

ORD record
ord-36743b9b689d4a9dbc65f524433382d2
Source dataset
uspto-grants-2007_03
Patent number
US07189850B2

Linked notes

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