Isopropyl iodide → HCID 66876886, compound

HRID 1666418Notes

Reaction equation

HRID 1666418 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[N:6][CH:7]=1.[CH:29](I)([CH3:31])[CH3:30].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH:29]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14]2)=[N:6][CH:7]=1)([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 66875736tert-Butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Product 1

HCID 66876886HCID 66876886, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of tert-butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.6 g, 1.56 mmol) in acetone (5 mL) cooled to 0° C. was added isopropyliodide (0.33 g, 1.96 mmol) and K2CO3 (0.43 g, 3.12 mmol). The reaction mixture was stirred at 80° C. overnight. The reaction mixture was evaporated to dryness and water (10 mL) was added and the mixture was extracted with ethyl acetate three times. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (1:19 acetone:hexane) to give the title compound (0.5 g, 75%). 1H NMR (500 MHz, CDCl3): δ 7.86 (d, J=3.3 Hz, 1H), 7.28 (m, 2H), 6.96 (d, J=7.5 Hz, 1H), 6.91 (m, 2H), 6.84 (d, J=8.5 Hz, 1H), 6.32 (s, 1H), 4.45 (m, 1H), 3.49 (m, 2H), 3.38 (m, 2H), 2.45 (m, 2H), 2.31 (m, 2H), 1.47 (s, 9H), 1.33 (d, J=6 Hz, 6H); m/z (425.2, M+ H+).

Workup

  1. customThe reaction mixture was evaporated to dryness and water (10 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate three times
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (1:19 acetone:hexane)

Sources & evidence

ORD record
ord-d4df9589f6104204a37796e0401e303a
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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