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

HRID 617425Notes

Reaction equation

HRID 617425 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 15 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 16 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-82019a429d3944cd93bc990b4d7417d2
Source dataset
uspto-grants-1999_09
Patent number
US05948886

Reaction notes

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