Potassium Hydroxide → 5,6-dihydro-2-[4-[3-(4-piperidinyl)propoxy]phenyl]-4H-1,3-oxazine

HRID 484492Notes

Reaction equation

HRID 484492 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][N:3]=[C:2]1[C:7]1[CH:27]=[CH:26][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18](C(OCC)=O)[CH2:17][CH2:16]2)=[CH:9][CH:8]=1.[OH-].[K+]>CC(O)C>[NH:18]1[CH2:19][CH2:20][CH:15]([CH2:14][CH2:13][CH2:12][O:11][C:10]2[CH:26]=[CH:27][C:7]([C:2]3[O:1][CH2:6][CH2:5][CH2:4][N:3]=3)=[CH:8][CH:9]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14989203ethyl 4-[3-[4-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenoxy]propyl]-1-piperidinecarboxylate

Product 1

HCID 149892045,6-dihydro-2-[4-[3-(4-piperidinyl)propoxy]phenyl]-4H-1,3-oxazineYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of ethyl 4-[3-[4-(5,6-dihydro-4H-1,3-oxazin-2-yl)phenoxy]propyl]-1-piperidinecarboxylate, 26,3 parts of potassium hydroxide and 200 parts of 2-propanol was stirred and refluxed for 3 hours. After evaporation, water was added ant eh solvent was distilled off till all traces of 2-propanol were removed. After cooling, ice water was added to the product was extracted with dichloromethane. The organic layer was dried, filtered and evaporated, yielding 14.5 parts (100%) of 5,6-dihydro-2-[4-[3-(4-piperidinyl) propoxy]phenyl]-4H-1,3-oxazine as a residue (int. 60).

Workup

  1. temperaturerefluxed for 3 hours
  2. customAfter evaporation, water
  3. additionwas added ant eh solvent
  4. distillationwas distilled off till all traces of 2-propanol
  5. customwere removed
  6. temperatureAfter cooling
  7. additionice water was added to the product
  8. extractionwas extracted with dichloromethane
  9. customThe organic layer was dried
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-abdcf5f7227f4524bf2811fd04bf8578
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

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