Acetic Acid → HCID 22603068, compound

HRID 2307855Notes

Reaction equation

HRID 2307855 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([NH:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.O.[C:22](O)(=O)[CH3:23]>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([NH:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[C:10]([C:3]3[CH2:4][CH2:5][NH:8][CH2:22][CH:23]=3)=[CH:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 962WaterHCID 22603069HCID 22603069, compound

Product 1

HCID 22603068HCID 22603068, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of 1-(4-Fluorophenyl)-N-methyl-1H-indole-5-carboxamide (3) (12.3 g) in a mixture of acetic acid (60 mL) and trifluoroacetic acid (15 rnL) was added during 0.5 h to a refluxing solution of 4-piperidon, HCl, H2O (36.6 g) in a mixture of acetic acid (50 mL) and trifluoroacetic acid (100 mL). The reaction mixture was refluxed for 1h, cooled to room temperature and the solvents were removed in vacuo. Water was added and pH was adjusted to 10 by addition of aqueous NaOH. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water and brine and dried over MgSO4. Evaporation of the solvents in vacuo afforded the title compound as a foam.Yield 16 g. 1H-NMR (DMSO) 2.48 (s, broad, 2H), 2.80 (d. 3H), 2.98 (t, 2H), 3.50 (d, 2H), 6.40(s, 1H) 7.45 (t, 2H), 7.50 (d, 1H), 7.65 (dd, 2H), 7.70-7.80 (m, 2H), 8.40 (s, 1H), 8.45 (q, broad, 1H)

Workup

  1. customthe solvents were removed in vacuo
  2. additionWater was added
  3. additionpH was adjusted to 10 by addition of aqueous NaOH
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washThe combined organic phases were washed with water and brine
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvents in vacuo

Sources & evidence

ORD record
ord-8146025f930b42cfb35c5a35f78be3da
Source dataset
uspto-grants-2004_12
Patent number
US06833376B2

Reaction notes

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