Sodium hydride → HCID 86600818, compound

HRID 736567Notes

Reaction equation

[H-].[Na+].[CH2:3]([C:5]1([CH3:26])[CH:10]([CH3:11])[C:9](=[N:12][OH:13])[CH2:8][C:7]([CH2:15][CH3:16])([CH3:14])[N:6]1[O:17][CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[CH3:4].[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][CH2:31]Cl>CN(C=O)C>[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][CH2:31][O:13][N:12]=[C:9]1[CH2:8][C:7]([CH2:15][CH3:16])([CH3:14])[N:6]([O:17][CH:18]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH3:19])[C:5]([CH2:3][CH3:4])([CH3:26])[CH:10]1[CH3:11]

Participants

Conditions

Temperature: 25 °C

Procedure

To a slurry of sodium hydride (4.36 g, 0.1 mol, 55% in mineral oil) in DMF (30 ml) is added dropwise the solution of 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidine-4-one oxime (16.6 g, 0.05 mol, prepared as described in WO 02/100831 A1). The mixture is stirred 150 min at 25° C. and then 3-dimethylaminopropylchloride (9.48 g, 0.06 mol) is added during 1 h. The mixture is stirred at room temperature for 18 h, the DMF is then evaporated in vacuo. The residue is dissolved in ethyl acetate (100 ml), washed with water (2×25 ml), dried over MgSO4 and evaporated. Chromatography on silica gel column (hexane-ethylacetate 1:1) affords 12.55 g of the title compound as a colorless oil.

Workup

stirringThe mixture is stirred at room temperature for 18 h
customthe DMF is then evaporated in vacuo
dissolutionThe residue is dissolved in ethyl acetate (100 ml)
washwashed with water (2×25 ml)
dry with materialdried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-c2b8b32298494a2ca8b233e252c73923
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595359B2

Reaction notes

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