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Morpholine → 2-(Ethyl(methyl)amino)-4-methyl-6-morpholino-pyridine-3-carboxylic acid ethylester

HRID 1039768
Notes
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Reaction equation

HRID 1039768 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:14]([CH2:16][CH3:17])[CH3:15])=[N:8][C:9](Cl)=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>[OH-].[Na+].CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:14]([CH2:16][CH3:17])[CH3:15])=[N:8][C:9]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8083MorpholineHCID 866643246-Chloro-2-(ethyl(methyl)amino)-4-methyl-pyridine-3-carboxylic acid ethylester

Product 1

HCID 672872702-(Ethyl(methyl)amino)-4-methyl-6-morpholino-pyridine-3-carboxylic acid ethylesterYield 41%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium Hydroxide
Solvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4.0 g (15.6 mmol) 6-chloro-2-(ethyl(methyl)amino)-4-methyl-pyridine-3-carboxylic acid ethylester and 13.6 ml (155.8 mmol) morpholine was heated in the MW to 135° C. for 2 h. Then the mixture was diluted with a 1M aq. NaOH sol. and EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 2.0 g (6.4 mmol, 41%) 2-(ethyl(methyl)amino)-4-methyl-6-morpholino-pyridine-3-carboxylic acid ethylester.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by CC (hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-107f41c8fed04809a6818e96a0e89f69
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552200B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes