4-Amino-1-methylpiperidine → N-(N-methyl-4-piperidinyl)-9-xanthenylamine

HRID 1415547Notes

Reaction equation

HRID 1415547 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][N:23]([CH3:26])[CH2:22][CH2:21]1>C1C=CC=CC=1>[CH3:26][N:23]1[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][CH2:22]1

Participants

4

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 125434549-Acetoxyxanthene

Product 1

HCID 21482845N-(N-methyl-4-piperidinyl)-9-xanthenylamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4.0 g. of 9-acetoxyxanthene and 1.9 g. of 4-amino-1-methylpiperidine in 100 ml. of dry benzene was refluxed for 24 hours. The cooled solution was then washed with 5% aqueous sodium carbonate solution and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue crystallized on triturating with hexane and was recrystallized from hexane to give N-(N-methyl-4-piperidinyl)-9-xanthenylamine, m.p. 96.5°-98° C.

Workup

  1. washThe cooled solution was then washed with 5% aqueous sodium carbonate solution
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue crystallized
  6. customon triturating with hexane
  7. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-24ab40c942164b57ba21fc04a8375798
Source dataset
uspto-grants-1977_01
Patent number
US04005208

Reaction notes

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