Potassium Hydroxide → HCID 12042434, compound

HRID 973962Notes

Reaction equation

HRID 973962 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([NH2:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O.Cl.[NH:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.[OH-].[K+]>CO>[NH:15]1[CH2:16][CH:17]=[C:18]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[C:6]([C:10]([NH2:12])=[O:11])[CH:5]=3)[NH:1][CH:2]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2723901PiperonylamineHCID 149732201H-Indole-5-carboxamide

Product 1

HCID 12042434HCID 12042434, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1H-indole-5-carboxamide (1.8 g), 4-piperidone hydrochloride monohydrate (3.4 g), and potassium hydroxide (11 g) in methanol (100 ml) was heated at reflux for 16 h. The mixture was cooled, and partitioned between ethyl acetate (200 ml) and saturated potassium carbonate (200 ml). The aqueous phase was separated, and extracted with ethyl acetate (100 ml. The organic extracts were combined, dried and the solvent evaporated in vacuo to give a semi-solid which was triturated with absolute ethanol (10 ml), and washed with ether (3×20 ml). The resultant solid was dried in vacuo to give the title compound, (1.1 g) m.p. 225°-230°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. temperatureThe mixture was cooled
  4. custompartitioned between ethyl acetate (200 ml) and saturated potassium carbonate (200 ml)
  5. customThe aqueous phase was separated
  6. extractionextracted with ethyl acetate (100 ml
  7. customdried
  8. customthe solvent evaporated in vacuo
  9. customto give a semi-solid which
  10. customwas triturated with absolute ethanol (10 ml)
  11. washwashed with ether (3×20 ml)
  12. customThe resultant solid was dried in vacuo

Sources & evidence

ORD record
ord-a78e15704776406597a4ecc4141da95a
Source dataset
uspto-grants-1991_11
Patent number
US05066660

Reaction notes

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