Sodium ethoxide → HCID 19773558, compound

HRID 1614322Notes

Reaction equation

HRID 1614322 reaction equation
[OH:1][NH:2][C:3](=[NH:6])[CH2:4][CH3:5].[O-]CC.[Na+].Cl.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][O:20][C:21]2[CH:31]=[CH:30][C:24]([C:25](OCC)=O)=[CH:23][CH:22]=2)[CH2:14][CH2:13]1>C(O)C>[CH2:4]([C:3]1[N:6]=[C:25]([C:24]2[CH:23]=[CH:22][C:21]([O:20][CH2:19][CH2:18][CH:15]3[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]3)=[CH:31][CH:30]=2)[O:1][N:2]=1)[CH3:5]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 19773535HCID 19773535, compoundHCID 178458070HCID 178458070, compound

Product 1

HCID 19773558HCID 19773558, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.0 parts of N-hydroxypropanimidamide, 2.9 parts of sodiumethoxide, 94.8 parts of ethanol and 25.3 parts of molecular sieve was stirred for 15 min. at room temperature. There were added 7.5 parts of ethyl 4-[2-(4-piperidinyl)ethoxy]benzoate monohydrochloride and stirring was continued for 12 hours at reflux temperature. The cooled reaction mixture was filtered and the filtrate was evaporated. The residue was partitioned between water and dichloromethane. The organic layer was separated, dried, filtered and evaporated, yielding 6.5 parts (89.9%) of 4-[2-[4-(3-ethyl-1,2,4-oxadiazol-5-yl)phenoxy]ethyl]piperidine (interm. 7).

Workup

  1. stirringstirring
  2. waitwas continued for 12 hours
  3. temperatureat reflux temperature
  4. customThe cooled reaction mixture
  5. filtrationwas filtered
  6. customthe filtrate was evaporated
  7. customThe residue was partitioned between water and dichloromethane
  8. customThe organic layer was separated
  9. customdried
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-c6354c05cf604b36aabd8a56e4e7b4a6
Source dataset
uspto-grants-1993_03
Patent number
US05196535

Reaction notes

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