Piperidine → HCID 21563690, compound

HRID 1730954Notes

Reaction equation

HRID 1730954 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:12]1([CH3:27])[CH:17]=[CH:16][C:15]([C:18]2[N:22]=[C:21]([CH2:23][C:24](O)=[O:25])[O:20][N:19]=2)=[CH:14][CH:13]=1.N1CCCCC1>C(O)C>[CH3:11][O:10][C:8]1[CH:9]=[C:2]2[C:3]([CH:4]=[C:23]([C:21]3[O:20][N:19]=[C:18]([C:15]4[CH:16]=[CH:17][C:12]([CH3:27])=[CH:13][CH:14]=4)[N:22]=3)[C:24](=[O:25])[O:1]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 21494400HCID 21494400, compound

Product 1

HCID 21563690HCID 21563690, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.5 parts of 2-hydroxy-4-methoxy benzaldehyde and 7.38 parts of the ethyl ester of 3-p-tolyl-1,2,4-oxadiazol-5-acetic acid (melting point: 56° C) are dissolved in 80 parts of ethanol. 0.3 part of piperidine is added and the mixture is heated for 1 hour under reflux. After cooling, the crystalline precipitate obtained is filtered and washed in ethanol. Thus 8.5 parts of 7-methoxy-3-(3-p-tolyl-1,2,4-oxadiazol-5-yl) coumarin are obtained which melts at 227° C.

Workup

  1. temperaturethe mixture is heated for 1 hour
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customthe crystalline precipitate obtained
  5. filtrationis filtered
  6. washwashed in ethanol

Sources & evidence

ORD record
ord-f21d340476be430997e18daa1c8b9974
Source dataset
uspto-grants-1976_11
Patent number
US03994907

Reaction notes

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