Dimethyl-(2-piperidin-2-yl-ethyl)-amine → 1-(9-Xanthenyl)-2-(2-dimethylaminoethyl)piperidine

HRID 1576393Notes

Reaction equation

HRID 1576393 reaction equation
[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][NH:6]1.C(O[CH:16]1[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:23][C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)(=O)C>C1C=CC=CC=1>[CH:18]1[C:17]2[CH:16]([N:6]3[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH3:11])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:23][C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 296295Dimethyl-(2-piperidin-2-yl-ethyl)-amineHCID 125434549-Acetoxyxanthene

Product 1

HCID 215125501-(9-Xanthenyl)-2-(2-dimethylaminoethyl)piperidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3.12 g. (0.02 mole) of 2-(2-dimethylaminoethyl)piperidine and 4.8 g. (0.02 mole) of 9-acetoxyxanthene in 75 ml. of anhydrous benzene was refluxed for 20 hours. The cooled solution was washed with 100 ml. of a 5 percent aqueous sodium bicarbonate solution, dried over anhydrous potassium carbonate, filtered, and evaporated in vacuo. The residue was taken up in low boiling petroleum ether and filtered to remove dixanthenyl ether. The filtrate was chromatographed on 125 g. of alumina, eluting successively with petroleum ether, petroleum etherbenzene mixtures, benzene, and finally ether. Evaporation of the ether fractions gave 1-(9-xanthenyl)-2-(2-dimethylaminoethyl)piperidine, m.p. 64°-67°C.

Workup

  1. washThe cooled solution was washed with 100 ml
  2. dry with materialof a 5 percent aqueous sodium bicarbonate solution, dried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. filtrationfiltered
  6. customto remove dixanthenyl ether
  7. customThe filtrate was chromatographed on 125 g
  8. washof alumina, eluting successively with petroleum ether, petroleum etherbenzene mixtures, benzene, and finally ether
  9. customEvaporation of the ether fractions

Sources & evidence

ORD record
ord-613d4b6d8ccd46bf882576d6fb7b57c2
Source dataset
uspto-grants-1976_09
Patent number
US03980788

Reaction notes

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