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

HRID 981626Notes

Reaction equation

HRID 981626 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 and the solvent was distilled off till all traces of 2-propanol were removed. After cooling, ice water was added and 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
  4. distillationthe solvent was distilled off till all traces of 2-propanol
  5. customwere removed
  6. temperatureAfter cooling
  7. additionice water was added
  8. extractionthe product was extracted with dichloromethane
  9. customThe organic layer was dried
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-f46b7d4db3014cfba7cb2ea0496ca1f8
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

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