Ethyl Acetate → 4-[4-Chloro-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-ylmethyl]-2,2-dimethyl-morpholine

HRID 251639Notes

Reaction equation

HRID 251639 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH2:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:16][CH3:17])[N:5]=[C:4]([CH3:18])[C:3]=1[CH2:19]Cl.[CH3:21][C:22]1([CH3:28])[O:27][CH2:26][CH2:25][NH:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CC#N.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH2:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:16][CH3:17])[N:5]=[C:4]([CH3:18])[C:3]=1[CH2:19][N:24]1[CH2:25][CH2:26][O:27][C:22]([CH3:28])([CH3:21])[CH2:23]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 189596742,2-DimethylmorpholineHCID 596781484-Chloro-3-chloromethyl-6-(2,6-diethyl-phenyl)-2-methyl-pyridine

Product 1

HCID 596782124-[4-Chloro-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-ylmethyl]-2,2-dimethyl-morpholine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-3-chloromethyl-6-(2,6-diethyl-phenyl)-2-methyl-pyridine (310 mg, 1.0 mmol), 2,2-dimethyl-morpholine (150 mg, 1.3 mmol) and K2CO3 (417 mg, 3 mmol) in CH3CN (10 mL) is stirred at room temperature for 16 hours. EtOAc (20 mL) and water (20 ml) are added to the mixture. The organic layer is separated, washed once with brine, dried (Na2SO4) and concentrated to give the title compound.

Workup

  1. customThe organic layer is separated
  2. washwashed once with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f15086e44a1042e8a4b3e5eb5f4508b1
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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