Hydrochloric Acid → HCID 57127353, compound

HRID 1899873Notes

Reaction equation

[CH3:1][C:2]([C:4]1[CH:15]=[CH:14][C:7]2[N:8]([CH2:12][CH3:13])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=1)=[O:3].[CH:16]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19]1)=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl>O1CCCC1.O>[CH2:12]([N:8]1[C:7]2[CH:14]=[CH:15][C:4]([C:2](=[O:3])[CH:1]=[CH:16][CH:18]3[CH2:19][CH2:20][N:21]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:22][CH2:23]3)=[CH:5][C:6]=2[N:10]=[C:9]1[CH3:11])[CH3:13]

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 0.1 g (0.5 mM) of 1-ethyl-2-methylbenzimidazole-5-yl methyl ketone and 0.1 g (0.5 mM) 4-formyl-N-benzylpiperidine in 10 mL of tetrahydrofuran (THF) was cooled to -78° C. under a nitrogen atmosphere. To this mixture were added dropwise 0.5 mL (0.5 mM) of a 1M solution of lithium bis (trimethylsilyl) amide in THF. The reaction was stirred at -78 ° C. for 1 hour, then warmed to room temperature. To the reaction was added 10 mL of water and the pH was adjusted to 2.0 with 1N hydrochloric acid (HCl). The mixture was extracted with 15 mL of ethyl acetate. The pH of the water layer was then sequentially adjusted to 3.0, 4.0, 5.0, 6.5, and 8.5 with 1N NaOH, each time extracting with 15 mL of ethyl acetate. The ethyl acetate extracts at pH=5.0 and 6.5 were combined, dried with sodium sulfate (Na2SO4) and evaporated to yield 50 mg (26%) of the title compound as an oil.

Workup

temperaturewarmed to room temperature
extractionThe mixture was extracted with 15 mL of ethyl acetate
extractioneach time extracting with 15 mL of ethyl acetate
dry with materialdried with sodium sulfate (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-f2aadb00bb9849749182cb21406543b3
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05574046

Reaction notes

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