Triethylamine → 3-morpholin-4-yl-N-pyridin-2-ylmethyl-propionamide

HRID 1783784Notes

Reaction equation

HRID 1783784 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]([O:11]C)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].C(Cl)(=O)C(Cl)=O.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)CC)C>CO.ClCCl>[N:1]1([CH2:7][CH2:8][C:9]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[O:11])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 195092-PyridinemethanamineHCID 65578Oxalyl chlorideHCID 1013734-Morpholinepropanoic acid, methyl ester

Product 1

HCID 688297333-morpholin-4-yl-N-pyridin-2-ylmethyl-propionamideYield 79.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-morpholinepropionate (5.0 g, 28.9 mmol) in MeOH (25 mL) was added 2N NaOH (17.3 mL, 34.6 mmol). The mixture was stirred for 1 h then concentrated in vacuo. The residue was suspended in dichloromethane (125 mL) and DMF (30 μL) was added followed by oxalylchloride (10 mL, 115.6 mmol). The mixture was allowed to stir for 2 h. then concentrated in vacuo. The resulting solid was added portion-wise to a solution of 2-(aminomethyl)pyridine (2.88 mL, 28.2 mmol) and triethylamine (9.0 mL, 64.86 mmol) in dichloromethane (200 mL). The mixture was stirred at ambient temperature for 1 h. then washed with water (300 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to yield 3-morpholin-4-yl-N-pyridin-2-ylmethyl-propionamide (5.56 g, 77%).

Workup

  1. concentrationthen concentrated in vacuo
  2. additionDMF (30 μL) was added
  3. stirringto stir for 2 h.
  4. concentrationthen concentrated in vacuo
  5. stirringThe mixture was stirred at ambient temperature for 1 h.
  6. washthen washed with water (300 mL)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5233a06d34af41338ead7aec562398df
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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