9-Acetoxyxanthene → N-methyl-N-(N-ethyl-3-piperidinyl)-9-xanthenylamine

HRID 1415546Notes

Reaction equation

HRID 1415546 reaction equation
C(O[CH:5]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:12][C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)(=O)C.[CH2:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([NH:27][CH3:28])[CH2:22]1)[CH3:20]>C1C=CC=CC=1>[CH3:28][N:27]([CH:5]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[O:12][C:13]2[C:18]1=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:23]1[CH2:24][CH2:25][CH2:26][N:21]([CH2:19][CH3:20])[CH2:22]1

Participants

4

Reactant 2

HCID 125434549-AcetoxyxantheneHCID 214828091-Ethyl-3-methylaminopiperidine

Product 1

HCID 21482827N-methyl-N-(N-ethyl-3-piperidinyl)-9-xanthenylamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3.7 g. (15.4 mmoles) of 9-acetoxyxanthene and 2.2 g. (15.5 mmoles) of 1-ethyl-3-methylaminopiperidine in 80 ml. of benzene was refluxed under nitrogen for 22.5 hours. It was then cooled to room temperature, washed with aqueous sodium bicarbonate solution, and dried over potassium carbonate. After removal of solvent in vacuo, the residue was dissolved in 25 ml. of petroleum ether and filtered from a small amount of crystals. The filtrate was then concentrated in vacuo and chromatographed on silica gel (ether solvent) to give N-methyl-N-(N-ethyl-3-piperidinyl)-9-xanthenylamine.

Workup

  1. washwashed with aqueous sodium bicarbonate solution
  2. dry with materialdried over potassium carbonate
  3. customAfter removal of solvent in vacuo
  4. dissolutionthe residue was dissolved in 25 ml
  5. filtrationof petroleum ether and filtered from a small amount of crystals
  6. concentrationThe filtrate was then concentrated in vacuo
  7. customchromatographed on silica gel (ether solvent)

Sources & evidence

ORD record
ord-db5e2acb19934cfd9b687be4999bda80
Source dataset
uspto-grants-1977_01
Patent number
US04005208

Reaction notes

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