Isopropyl iodide → HCID 59442121, compound
Reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:18]2[CH2:23][NH:22][CH2:21][CH2:20][CH:19]=2)[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16].I[CH:25]([CH3:27])[CH3:26]>C(#N)C>[CH3:26][CH:25]([N:22]1[CH2:23][C:18]([C:11]2[CH:12]=[CH:13][C:14]([N+:15]([O-:17])=[O:16])=[C:9]([O:8][CH3:7])[CH:10]=2)=[CH:19][CH2:20][CH2:21]1)[CH3:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
To a pressure vessel containing acetonitrile (40 mL) and potassium carbonate (4.0 g, 29.2 mmol) was added 5-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine (1.7 g, 7.3 mmol) and 2-iodopropane (1.85 g, 10.9 mmol). The reaction was stirred at 85° C. overnight. After removal of the solvent under reduced pressure the residue was diluted with ethyl acetate (30 mL) and washed with water (40 mL). After partitioning and extraction of the aqueous layer (Ethyl acetate 2×15 mL), the organic layer was dried over sodium sulfate, filtered, concentrated and purified via chromatography on SiO2 to afford 1-(1-methylethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine (1.6 g, 80% yield.) ESIMS (M+H)+=277.1.
Workup
- customAfter removal of the solvent under reduced pressure the residue
- additionwas diluted with ethyl acetate (30 mL)
- washwashed with water (40 mL)
- customAfter partitioning
- extractionextraction of the aqueous layer (Ethyl acetate 2×15 mL)
- dry with materialthe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified via chromatography on SiO2
Sources & evidence
- ORD record
- ord-491667614fe141419a426ae075855ea9
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981903B2
Reaction notes
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