Water → HCID 22165605, compound

HRID 1032345Notes

Reaction equation

HRID 1032345 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33]>O1CCCC1.CCOCC.CC(C)=O>[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33].[C:1]1([CH:7]([C:32]2[CH:31]=[CH:3][CH:2]=[CH:1][CH:6]=2)[O:8][CH2:9][CH2:10][N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 962WaterHCID 971Oxalic AcidHCID 21226445Aluminium lithium hydrideHCID 22165607HCID 22165607, compound

Product 1

HCID 22165605HCID 22165605, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3 g (7.78 mmole) of 1-[(phenylmethoxy)acetyl]-3-phenylpiperidine in 30 cm3 of tetrahydrofuran was added dropwise to a solution of 0.5 g (12.4 mmole) of lithium aluminum hydride in 50 cm3 of tetrahydrofuran. The mixture was heated to reflux for 4 hours, left overnight, and then hydrolyzed by the addition of 2.5 cm3 of water. It was diluted with 100 cm3 of ether. The alkaline sediments are separated and washed with ether. The ethereal phases were collected, dried on sodium sulfate and concentrated under reduced pressure. The residue was dissolved in 20 cm3 of acetone. A solution of 0.75 g (8.3 mmole) of oxalic acid in 30 cm3 of acetone was added. The oxalate precipitate was filtered, and recrystallized from acetone.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe alkaline sediments are separated
  4. washwashed with ether
  5. customThe ethereal phases were collected
  6. customdried on sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in 20 cm3 of acetone
  9. filtrationThe oxalate precipitate was filtered
  10. customrecrystallized from acetone

Sources & evidence

ORD record
ord-ae199f1fc4a349329b47d1b555f313d4
Source dataset
uspto-grants-1990_09
Patent number
US04957927

Reaction notes

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