Water → 1-[2-(Diphenylmethoxy)ethyl]-3-(3-methoxyphenyl)piperidine oxalate

HRID 1032348Notes

Reaction equation

HRID 1032348 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[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][C:19]=3OC)[CH2:13]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[C:39]([OH:44])(=[O:43])[C:40]([OH:42])=[O:41]>O1CCCC1.CC(C)=O>[C:39]([OH:44])(=[O:43])[C:40]([OH:42])=[O:41].[C:26]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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]=[C:20]([O:41][CH3:40])[CH:19]=3)[CH2:13]2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 962WaterHCID 971Oxalic AcidHCID 21226445Aluminium lithium hydrideHCID 221656081-[(Diphenylmethoxy)acetyl]-3-(methoxyphenyl)piperidine

Product 1

HCID 221656101-[2-(Diphenylmethoxy)ethyl]-3-(3-methoxyphenyl)piperidine oxalate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.6 g (15.9 mmole) of 1-[(diphenylmethoxy)acetyl]-3-(methoxyphenyl)piperidine in 50 cm3 of tetrahydrofuran was added dropwise to a solution of 0.96 g (25.4 mmole) of lithium aluminum hydride in 100 cm3 of tetrahydrofuran. The mixture was brought to reflux for 5 hours, allowed to stand overnight, then hydrolyzed by the addition of 5 cm3 of water. The alkaline residues were separated. The solution was concentrated under reduced pressure. The residue was treated with a solution of 1.5 g (16.7 mmole) of oxalic acid in 100 cm3 of acetone. The 1-[2-(diphenylmethoxy)ethyl]-3-(3-methoxyphenyl)piperidine oxalate precipitate was filtered and recrystallized from acetone.

Workup

  1. temperatureto reflux for 5 hours
  2. customThe alkaline residues were separated
  3. concentrationThe solution was concentrated under reduced pressure
  4. filtrationThe 1-[2-(diphenylmethoxy)ethyl]-3-(3-methoxyphenyl)piperidine oxalate precipitate was filtered
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-44254b69448844958c1fbe47496468de
Source dataset
uspto-grants-1990_09
Patent number
US04957927

Reaction notes

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