Water → N-Methyl-N-(4-((2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl)phenyl)pyridin-2-amine

HRID 424427Notes

Reaction equation

HRID 424427 reaction equation
[C:1]1([C@H:7]([N:9]2[CH2:14][CH2:13][O:12][C@@H:11]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[CH:17][CH:16]=3)[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.IC.[CH3:30]C(C)([O-])C.[K+].O>O1CCCC1>[CH3:30][N:21]([C:18]1[CH:19]=[CH:20][C:15]([C@@H:11]2[O:12][CH2:13][CH2:14][N:9]([C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH3:8])[CH2:10]2)=[CH:16][CH:17]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 66703932HCID 66703932, compound

Product 1

HCID 66703976N-Methyl-N-(4-((2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl)phenyl)pyridin-2-amineYield 101.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-((2S)-4-((1R)-1-phenylethyl)morpholin-2-yl)phenyl)pyridin-2-amine (0.57 g, 1.5 mmol) and iodomethane (1.6 g, 11.2 mmol) in tetrahydrofuran (50 ml) was added potassium tert-butoxide (1.6 g, 9.45 mmol). After stirring at room temperature for 4 hours, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated. The crude product was purified by column chromatography on silica gel (hexane-ethyl acetate, 1:1) to afford N-Methyl-N-(4-((2S)-4-((1R)-1-phenylethyl)-morpholin-2-yl)phenyl)pyridin-2-amine (0.57 g, 81%) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe crude product was purified by column chromatography on silica gel (hexane-ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-e3bcdf3ffc5d45979dbe9424b654d974
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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