Water → HCID 21453220, compound

HRID 436602Notes

Reaction equation

HRID 436602 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:9]=1[O:10][CH2:11][CH2:12][C:13]([N:15]1[CH2:31][CH2:30][C:18]2([N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:21][NH:20][C:19]2=[O:29])[CH2:17][CH2:16]1)=O.O1CCCC1.O>C(Cl)(Cl)Cl>[Cl:7][C:8]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][N:15]1[CH2:16][CH2:17][C:18]2([N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:21][NH:20][C:19]2=[O:29])[CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 21453230HCID 21453230, compound

Product 1

HCID 21453220HCID 21453220, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 0.4 g of lithium aluminum hydride, 2.2 g of 8-{3-(2-chloro-4-fluorophenoxy)propionyl}-1-phenyl-4-oxo-1,3,8-triazaspiro[4,5]decane and 40 ml of tetrahydrofuran was heated under reflux for 3 hours. To the reaction mixture were added gradually water and chloroform under cooling, and the precipitate was filtered off. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The residue was triturated with ether, cooled and filtered to give 8-{3-(2-chloro-4-fluorophenoxy)propyl}-1-phenyl-4-oxo-1,3,8-triazaspiro-[4,5]decane, m.p. 154° - 155° C; recrystallized from benzenecyclohexane, m.p. 155° - 156° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureunder cooling
  4. filtrationthe precipitate was filtered off
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with ether
  9. temperaturecooled
  10. filtrationfiltered

Sources & evidence

ORD record
ord-eecbc6bdd2124d3cab5e2ebbaed930c9
Source dataset
uspto-grants-1977_02
Patent number
US04009275

Reaction notes

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