Imidazole → HCID 57588941, compound

HRID 1808741Notes

Reaction equation

HRID 1808741 reaction equation
CN(C)C=O.[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>O>[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([O:19][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:15][CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 57588941HCID 57588941, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a N,N-dimethylformamide (10 mL) solution of N-benzyl-4-hydroxypiperidine (1.90 g, 9.93 mmol) was added imidazole (1.35 g, 19.9 mmol) and tert-butyldimethylsilyl chloride (1.57 g, 10.4 mmol). After 1.5 hours, the reaction mixture was diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine (50 mL), dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound. 1H NMR (500 MHz, CDCl3) δ 7.36-7.21 (m, 5H), 3.75-3.65 (m, 1H), 3.49 (s, 2H), 2.72-2.63 (m, 2H), 2.26-2.12 (m, 2H), 1.78-1.71 (m, 2H), 1.62-1.53 (m, 2H), 0.88 (s, 9H), 0.04 (s, 6H); LC-MS: m/z 306.1 (M+H).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic extracts were washed with brine (50 mL)
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washChromatography over silica gel, eluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-c460ebb633c149098bcecf2d44324c6b
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

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