Water → 4-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridine

HRID 898950Notes

Reaction equation

HRID 898950 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11]C)=O)[CH:4]=1.[NH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.O>C1COCC1>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](=[O:11])[NH:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4082852-MorpholinoethylamineHCID 16655470Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 236145794-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridineYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-chloropyridine-2-carboxylate HCl salt (Method A2, Step 2; 1.01 g, 4.86 mmol) in THF (20 mL) was added 4-(2-aminoethyl)morpholine (2.55 mL, 19.4 mmol) dropwise and the resulting solution was heated at the reflux temp. for 20 h, cooled to room temp., and treated with water (50 mL). The resulting mixture was extracted with EtOAc (50 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 4-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridine as a yellow oil (1.25 g, 95%): TLC (10% MeOH/90% EtOAc) Rf 0.50.

Workup

  1. temperaturethe resulting solution was heated at the reflux temp
  2. temperaturecooled to room temp.
  3. extractionThe resulting mixture was extracted with EtOAc (50 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bcf8409be2247df829594bd3dd7b737
Source dataset
uspto-grants-2008_04
Patent number
US07351834B1

Reaction notes

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