Morpholine → 6-(Morpholine-4-carbonyl)nicotinic acid, t-butyl ester

HRID 613233Notes

Reaction equation

HRID 613233 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([O-:9])=[O:8])[CH:4]=[CH:3][C:2]=1[C:10]([O:12]C)=O.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>O1CCCC1>[N:14]1([C:10]([C:2]2[CH:3]=[CH:4][C:5]([C:7]([O:9][C:5]([CH3:7])([CH3:6])[CH3:4])=[O:8])=[CH:6][N:1]=2)=[O:12])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 425561312,5-Pyridinedicarboxylic acid, 2-methyl ester

Product 1

HCID 100857186-(Morpholine-4-carbonyl)nicotinic acid, t-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For example, the 2,5-pyridinedicarboxylic acid, 2-methyl ester, 5-t-butyl ester (11) is contacted with a molar excess of morpholine in an appropriate organic solvent, such as tetrahydrofuran. The reaction is typically conducted at a temperature range of from room temperature to reflux and for a period of time ranging from 5 hours to 3 days. The 6-(morpholine-4-carbonyl)nicotinic acid, t-butyl ester (12) is isolated from the reaction mixture by standard extractive methods as is known in the art and may be purified by crystallization.

Workup

  1. customis typically conducted at a temperature range of from room temperature
  2. temperatureto reflux and for a period of time
  3. waitranging from 5 hours to 3 days

Sources & evidence

ORD record
ord-e1e56a8925d9495baf0e37ec1db3f616
Source dataset
uspto-grants-1999_12
Patent number
US06008196

Reaction notes

Loading…