Water → HCID 22165613, compound

HRID 1032346Notes

Reaction equation

HRID 1032346 reaction equation
[C:1]1([CH:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[C:37]([OH:42])(=[O:41])[C:38]([OH:40])=[O:39]>O1CCCC1.CC(C)=O.CCOCC>[C:37]([OH:42])(=[O:41])[C:38]([OH:40])=[O:39].[C:1]1([CH:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:8][CH2:9][CH2:10][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:14][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 971Oxalic AcidHCID 14556326HCID 14556326, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22165613HCID 22165613, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.4 g (18.6 mmole) of 1-[(diphenylmethoxy) acetyl]-4-phenylpiperidine in 60 cm3 of tetrahydrofuran was added to a solution of 1.1 g (29.7 mmole) of lithium aluminum hydride in 100 cm3 of tetrahydrofuran. The mixture was heated to a reflux for 12 hours and, after cooling to room temperature, hydrolyzed with 5.5 cm3 of water. 200 cm3 of ether was added. The alkaline residues were washed with ether. The ethereal solutions were collected, dried on sodium sulfate and concentrated under reduced pressure. The residue was dissolved in 30 cm3 of acetone. A solution of 1.7 g (18.9 mmole) of oxalic acid in 150 cm3 of acetone was added. The 1-[2-(diphenylmethoxy)ethyl]-4-phenyl piperidine oxalate precipitate was filtered, then recrystallized from an acetone-ethanol mixture.

Workup

  1. temperatureThe mixture was heated to
  2. temperaturea reflux for 12 hours
  3. washThe alkaline residues were washed with ether
  4. customThe ethereal solutions were collected
  5. customdried on sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 30 cm3 of acetone
  8. filtrationThe 1-[2-(diphenylmethoxy)ethyl]-4-phenyl piperidine oxalate precipitate was filtered
  9. customrecrystallized from an acetone-ethanol mixture

Sources & evidence

ORD record
ord-7ffae5c6a87349b9b0a7debf4c44287d
Source dataset
uspto-grants-1990_09
Patent number
US04957927

Reaction notes

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