Morpholine → HCID 86714238, compound

HRID 1753269Notes

Reaction equation

HRID 1753269 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]=[C:4]([C:11]([OH:13])=[O:12])[CH:3]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>>[O:17]1[CH2:18][CH2:19][N:14]([C:2]2[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]=[C:4]([C:11]([OH:13])=[O:12])[CH:3]=2)[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 3040104-chloropyridine-2,6-dicarboxylic acid

Product 1

HCID 86714238HCID 86714238, compound

Conditions

Temperature
120 °C

Procedure

4-chloro-pyridine-2,6-dicarboxylic acid (0.025 mol, 5.0 g) is slowly added under stirring to a solution of morpholine (0.250 mol, 21.6 g) at room temperature. Care is taken to avoid a too-fast addition leading to local temperature increase. Precipitation of a solid is observed. The reaction mixture is heated at 120° C. for 2 hr. By gradually heating the reaction mixture becomes solid. After cooling at 60° C., H20 (80 ml) is added and the mixture is stirred for 30 min. until the solid is completely dissolved. The solution is then acidified with 2M HCl until pH=1. The formed precipitate is filtered, washed twice H2O and dried overnight at 70° C. (70%)

Workup

  1. additiona too-fast addition
  2. temperatureincrease
  3. customPrecipitation of a solid
  4. temperatureBy gradually heating the reaction mixture
  5. temperatureAfter cooling at 60° C.
  6. additionH20 (80 ml) is added
  7. dissolutionis completely dissolved
  8. filtrationThe formed precipitate is filtered
  9. washwashed twice H2O
  10. customdried overnight at 70° C. (70%)

Sources & evidence

ORD record
ord-494b39c12bc74a05b93afd0de4e7b1a7
Source dataset
uspto-grants-2015_10
Patent number
US09163155B2

Reaction notes

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