HCID 12319481, compound → HCID 12319489, compound

HRID 1077324Notes

Reaction equation

HRID 1077324 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:10]1[CH2:15][CH2:14][C:13]2([C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:16]2)[CH2:12][CH2:11]1)(=O)[CH3:8]>O1CCCC1>[CH2:7]([N:10]1[CH2:15][CH2:14][C:13]2([C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:16]2)[CH2:12][CH2:11]1)[CH3:8]

Participants

4

Reactant 2

HCID 12319481HCID 12319481, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12319489HCID 12319489, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 0.53 g. of lithium aluminum hydride in 50 ml. of tetrahydrofuran is added dropwise a solution of 2.20 g. of 1'-acetyl-1,3-dihydro-3-phenylspiro[isobenzofuran-1,4'-piperidine] (Example 80), in 50 ml. of tetrahydrofuran. The mixture is heated under reflux for 2 hours, cooled, quenched cautiously with water, and extracted with ether. The ether solution is dried over sodium sulfate and concentrated to a solid. Recrystallization from chloroform provides colorless crystals, m.p. 113°-115°.

Workup

  1. additionTo a stirred suspension of 0.53 g
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 2 hours
  4. temperaturecooled
  5. customquenched cautiously with water
  6. extractionextracted with ether
  7. dry with materialThe ether solution is dried over sodium sulfate
  8. concentrationconcentrated to a solid
  9. customRecrystallization from chloroform
  10. customprovides colorless crystals, m.p. 113°-115°

Sources & evidence

ORD record
ord-0a8bbf9b9e1b4671ad35ebe5d34e4d24
Source dataset
uspto-grants-1976_05
Patent number
US03959475

Reaction notes

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