Water → 4-[(6-Bromopyridin-2-yl)methyl]morpholine-3-carboxamide

HRID 385990Notes

Reaction equation

HRID 385990 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[N:3]=1.Cl.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH:12]1[C:17]([NH2:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([CH2:8][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH:12]2[C:17]([NH2:19])=[O:18])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 67166308Morpholine-3-carboxylic acid amide hydrochloride

Product 1

HCID 595255734-[(6-Bromopyridin-2-yl)methyl]morpholine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (150 mg, 0.60 mmol), morpholine-3-carboxamide hydrochloride (100 mg, 0.560 mmol) and potassium carbonate (207 mg, 1.50 mmol) were taken up in DMF (3 mL) and the reaction was maintained at room temperature overnight. Water was then added and the mixture was extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as an orange oil.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7cac246ef56c4f029533d89df39a7d61
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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