Sodium Hydroxide → HCID 178444679, compound

HRID 353125Notes

Reaction equation

HRID 353125 reaction equation
C(S[C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]([C:20]3([CH3:33])[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:22][CH:21]3[CH3:32])[CH:17]=[CH:18][CH:19]=2)[N:13]=1)C1C=CC=CC=1.[OH-].[Na+]>C(O)C.[Ni]>[CH2:26]([N:23]1[CH2:24][CH2:25][C:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:12]3[N:13]=[CH:9][NH:10][CH:11]=3)[CH:15]=2)([CH3:33])[CH:21]([CH3:32])[CH2:22]1)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178444680HCID 178444680, compound

Product 1

HCID 178444679HCID 178444679, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(3-(2-(benzylsulfanyl)-1H-imidazol-4-yl)phenyl)-1-hexyl-3,4-dimethylpiperidine (Example 51, 98 mg, 0.21 mmol) in ethanol (2 mL) at room temperature was added 1 N NaOH (1.5 mL) and Raney® nickel (0.5 g, 50% slurry in water). The reaction was stirred for 5 minutes and then filtered through Celite®, washing with ethanol. The filtrate was concentrated in vacuo and the residue was dissolved in ethyl acetate (5 mL). The organic layer was washed with saturated aqueous sodium hydrogencarbonate (5 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was then purified by column chromatography on silica gel eluting with ethyl acetate:0.88 ammonia (100:1) and then ethyl acetate:methanol:0.88 ammonia (70:30:1). The title compound was obtained as a clear oil (13 mg, 19%).

Workup

  1. filtrationfiltered through Celite®
  2. washwashing with ethanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (5 mL)
  5. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate (5 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was then purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-5d5cd87b84694131ad7e51674a79c432
Source dataset
uspto-grants-2004_06
Patent number
US06750231B2

Reaction notes

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