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4-(Methylamino)benzoic acid → UP9V9DB2RD

HRID 967775
Notes
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Reaction equation

HRID 967775 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:18][CH2:17][C:14]3([CH2:16][O:15]3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].[CH3:19][NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+]>FC(F)(F)S([O-])(=O)=O.[Sc+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(#N)C.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:18][CH2:17][C:14]([CH2:16][N:20]([CH3:19])[C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:28][CH:29]=3)([OH:15])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 663454-(Methylamino)benzoic acidHCID 516892Sodium BicarbonateHCID 858197211-[2-(4-Cyanophenyl)ethyl]piperidin-4-spiro-2'-oxirane

Product 1

HCID 12986481UP9V9DB2RDYield 64.5%

Reagents, catalysts & solvents 3

HCID 2734571Scandium(III) triflateCatalyst
HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent2×

Procedure

Scandium trifluoromethanesulfonate (609 mg) was added to a mixture of the compound (500 mg) obtained in Step 3 of Example 1, 4-methylaminobenzoic acid (343 mg) and anhydrous acetonitrile (10 mL) under cooling with ice-water, and the mixture was stirred at room temperature for sixty eight hours under nitrogen atmosphere. Water (50 mL) and acetonitrile (10 mL) were added to the resulting mixture and the pH of the mixture was adjusted to above 9 with sodium hydrogen carbonate, insoluble matter was removed by filtration and the filtrate was concentrated under reduced pressure. Water in the residue was removed by azeotrope with ethanol, soluble components in the residue were dissolved in ethanol and the insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure and then, the residue was dissolved in water (50 mL) and the pH of the solution was adjusted to 7 by diluted hydrochloric acid. Precipitate was collected by filtration and washed with water and ethyl acetate successively under stirring. The precipitate was collected by filtration and dried to obtain the titled compound (524 mg) as powder.

Workup

  1. customwas removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customWater in the residue was removed by azeotrope with ethanol, soluble components in the residue
  4. dissolutionwere dissolved in ethanol
  5. customthe insoluble matter was removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in water (50 mL)
  8. filtrationPrecipitate was collected by filtration
  9. washwashed with water and ethyl acetate successively
  10. stirringunder stirring
  11. filtrationThe precipitate was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-4299d678945a4105be6f8c2c05d2b8d2
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06956046B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes