Piperidine → 2-(N-Piperidinyl)-naphthacene-5,12-dione

HRID 275074Notes

Reaction equation

HRID 275074 reaction equation
F[C:2]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:21])[C:4]=2[CH:3]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[N:22]1([C:2]2[CH:19]=[CH:18][C:17]3[C:16](=[O:20])[C:15]4[C:6](=[CH:7][C:8]5[C:13]([CH:14]=4)=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:5](=[O:21])[C:4]=3[CH:3]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 200898282-Fluorotetracene-5,12-dione

Product 1

HCID 200898392-(N-Piperidinyl)-naphthacene-5,12-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1 g (3.62 mmol) of 2-fluoro-naphthacene-5,12-dione, 0.92 g (10.86 mmol) of piperidine, 1.50 g (10.86 mmol) of potassium carbonate and 10 ml of DMSO are stirred at a bath temperature of 60° C. for 45 minutes. After cooling, the mixture is poured onto water and the orange product is filtered off. The crystals are dissolved in tetrahydrofuran (THF)/toluene and the solution is dried over sodium sulfate and evaporated. The residue is recrystallized from toluene/pentane. Yield: 1.11 g (90%); melting point 230°-233° C.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is poured onto water
  3. filtrationthe orange product is filtered off
  4. dissolutionThe crystals are dissolved in tetrahydrofuran (THF)/toluene
  5. dry with materialthe solution is dried over sodium sulfate
  6. customevaporated
  7. customThe residue is recrystallized from toluene/pentane

Sources & evidence

ORD record
ord-23f03ffa8711420c8023b7867c65dc4d
Source dataset
uspto-grants-1995_02
Patent number
US05391749

Reaction notes

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