Water → HCID 70632561, compound

HRID 328564Notes

Reaction equation

HRID 328564 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([CH2:22][CH2:23][N:24]2[CH2:40][CH2:39][C:27]3([N:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:30][NH:29][C:28]3=[O:38])[CH2:26][CH2:25]2)=O)=[CH:15][CH:14]=1.O>C1C=CC=CC=1>[F:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][CH2:20][CH2:22][CH2:23][N:24]2[CH2:40][CH2:39][C:27]3([N:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:30][NH:29][C:28]3=[O:38])[CH2:26][CH2:25]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 53470106HCID 53470106, compound

Product 1

HCID 70632561HCID 70632561, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 4 g of lithium aluminum hydride and 40 ml of tetrahydrofuran was added portionwise 2 g of 8-{2-[N-(p-fluorophenyl)carbamoyl]ethyl}-1-phenyl-4-oxo-1, 3, 8-triazaspiro[4, 5]decane under cooling. Then, the mixture was heated under reflux for 4 hours. To the reaction mixture were gradually added water and benzene under cooling, and the precipitate was filtered off. The organic layer was separated, dried over sodium sulfate evaporated under reduced pressure. The residue was triturated with ether, cooled and filtered to give 8-{3-(p-fluoroanilino)propyl}-1-phenyl-4-oxo-1, 3, 8-triazaspiro[4, 5]decane, m.p. 158°-162° C; recrystallized from benzene, m.p. 177°-178° C.

Workup

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

Sources & evidence

ORD record
ord-7ce8998a9dec423dbf3ef36a4c25de6f
Source dataset
uspto-grants-1977_04
Patent number
US04017624

Reaction notes

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