3-amino-N-ethylpiperidine → HCID 21482860, compound

HRID 1415544Notes

Reaction equation

HRID 1415544 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.[NH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][N:22]([CH2:26][CH3:27])[CH2:21]1>C1(C)C=CC=CC=1>[CH2:26]([N:22]1[CH2:23][CH2:24][CH2:25][CH:20]([NH:19][CH:5]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[O:12][C:13]3[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:21]1)[CH3:27]

Participants

4

Reactant 2

HCID 980943-amino-N-ethylpiperidineHCID 125434549-Acetoxyxanthene

Product 1

HCID 21482860HCID 21482860, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4.0 g. of 9-acetoxyxanthene and 2.36 g. of 3-amino-1-ethylpiperidine in 175 ml. of dry toluene was refluxed for 24 hours. The cooled solution was then concentrated in vacuo. The residue was chromatographed on activated magnesium silicate, eluting with ether and acetone. Concentration of the acetone fraction in vacuo and then chromatographing on silica gel with acetone, then concentrating the eluate in vacuo gave N-(N-ethyl-3-piperidinyl)-9-xanthenylamine, m.p. 47.5°-48.5° C.

Workup

  1. concentrationThe cooled solution was then concentrated in vacuo
  2. customThe residue was chromatographed on activated magnesium silicate
  3. washeluting with ether and acetone
  4. concentrationConcentration of the acetone fraction in vacuo and then chromatographing on silica gel with acetone, then concentrating the eluate in vacuo

Sources & evidence

ORD record
ord-534b5c917b294b0bbbe0d4cdcfa1b493
Source dataset
uspto-grants-1977_01
Patent number
US04005208

Reaction notes

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