Sodium hydride → HCID 67265131, compound

HRID 1685143Notes

Reaction equation

HRID 1685143 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:10][CH2:9][N:8]([CH3:13])[CH3:6])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178451794HCID 178451794, compound

Product 1

HCID 67265131HCID 67265131, compoundYield 166.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Add 4-[4-(3,4-difluoro-phenyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (500 mg; 1.38 mmol) to a solution of NaH (110 mg; 2.76 mmol) in DMSO (50 mL) at 0° C., and stir for 1 h at RT. Add (N,N-dimethyl)ethyl chloride hydrochloride (238 mg; 1.65 mmol) to the resulting mixture and allow to stir at RT for 18 h. Monitor the reaction by thin layer chromatography (TLC). Quench the reaction mixture with ice water and extract with EA. Separate the organic layer, wash twice with brine (2×50 mL), dry over anhydrous Na2SO4 and evaporate under reduced pressure. Purify the residue by column chromatography on silica gel (60/120 mesh) using DCM:Methanol (98:2) as eluent to give 0.5 g (86%) of the title compound. LCMS=484(M+H).

Workup

  1. stirringto stir at RT for 18 h
  2. customMonitor the reaction by thin layer chromatography (TLC)
  3. customQuench the reaction mixture with ice water
  4. extractionextract with EA
  5. customSeparate the organic layer
  6. washwash twice with brine (2×50 mL)
  7. dry with materialdry over anhydrous Na2SO4
  8. customevaporate under reduced pressure
  9. customPurify the residue by column chromatography on silica gel (60/120 mesh)

Sources & evidence

ORD record
ord-00d774a071434f69943a58e44c1a1bf4
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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