Morpholine → HCID 178420829, compound

HRID 2254879Notes

Reaction equation

HRID 2254879 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])([CH3:4])([CH3:3])[CH3:2].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(O)(C)C>[NH2+:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.[C:22]([C:19]1[CH:18]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:20]=1[OH:21])[NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([O-:14])=[O:13])([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 601943-(3,5-DI-T-Butyl-4-hydroxyanilino)benzoic acid

Product 1

HCID 178420829HCID 178420829, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A mixture of 1.70g (0.005 mole) of 3-(3,5-di-tertiary-butyl-4-hydroxyanilino)benzoic acid (prepared in Example 13) and 50 ml of hot isopropyl alcohol was filtered to remove a small amount of insoluble material. The resulting solution was deoxygenated with a stream of nitrogen gas. Uner a nitrogen atmosphere, a solution of 0.44g (0.005 mole) of morpholine in 1.5 ml of isopropyl alcohol was added with rapid stirring. Evaporation provided a solid which was recrystallized from a mixture of isopropyl alcohol and isopropyl ether to give solid morpholinium-3-(3,5-di-tertiary-butyl-4-hydroxyanilino)benzoate, m.p. 147°-150° C. Analysis: Calculated for C21H27NOC4H9NO: %C, 70.1; %H, 8.5; %N, 6.5; Found: %C, 69.8; %H, 8.5; %N, 6.4.

Workup

  1. filtrationwas filtered
  2. customto remove a small amount of insoluble material
  3. customThe resulting solution was deoxygenated with a stream of nitrogen gas
  4. customEvaporation
  5. customprovided a solid which
  6. customwas recrystallized from a mixture of isopropyl alcohol and isopropyl ether

Sources & evidence

ORD record
ord-1b6b6031ae23435ba9b25ff9bfc525d9
Source dataset
uspto-grants-1993_08
Patent number
US05237070

Reaction notes

Loading…