HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 922041
Notes
Print preview

Reaction equation

HRID 922041 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-6bb2cde97d234e959d8a17b2fdc49199
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278103B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes