Quinizarin → 9,10-Anthracenedione, 1,4-bis((2-(1-piperidinyl)ethyl)amino)-

HRID 1719473Notes

Reaction equation

HRID 1719473 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:15](=[O:16])[C:14]3[C:9](=[C:10](O)[CH:11]=[CH:12][C:13]=3O)[C:7](=[O:8])[C:5]=2[CH:6]=1.[NH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>O>[N:22]1([CH2:21][CH2:20][NH:19][C:13]2[C:14]3[C:15](=[O:16])[C:4]4[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=4)[C:7](=[O:8])[C:9]=3[C:10]([NH:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:11][CH:12]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 6688QuinizarinHCID 33944N-(2-Aminoethyl)piperidine

Product 1

HCID 1526219,10-Anthracenedione, 1,4-bis((2-(1-piperidinyl)ethyl)amino)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.07 g. or quinizarin, 21.74 g. of N-(2-aminoethyl)piperidine and 26 ml. of water is stirred under reflux for 2 hours and then allowed to stand overnight. The gummy solid is collected and washed with water by centrifugation, giving 1.99 g. of blue-black solid. This solid is dissolved in 15 ml. of chloroform and chromatographed by an abbreviated wet-column procedure on 100 g. of alumina, eluting with chloroform. A total of 180 ml. of eluate is collected in eight separate cuts from the time the eluate turns blue until a black band nears the bottom of the column. Cuts 1-6 are combined and evaporated giving 1.42 g. of blue-black crystals which are recrystallized from ethanol giving 1.35 g. of the desired product as blue-black needles, mp. 140°-141° C. Product dried in vacuo at 78° C. melted at 156°-157° C.

Workup

  1. additionA mixture of 4.07 g
  2. temperatureunder reflux for 2 hours
  3. customThe gummy solid is collected
  4. washwashed with water by centrifugation
  5. customgiving 1.99 g
  6. dissolutionThis solid is dissolved in 15 ml
  7. customof chloroform and chromatographed by an abbreviated wet-column procedure on 100 g
  8. washof alumina, eluting with chloroform
  9. customof eluate is collected in eight
  10. customseparate cuts from the time the eluate
  11. customevaporated
  12. customgiving 1.42 g
  13. customof blue-black crystals which are recrystallized from ethanol giving 1.35 g
  14. customProduct dried in vacuo at 78° C. melted at 156°-157° C.

Sources & evidence

ORD record
ord-de3897879d8c40158dc7652958dd1684
Source dataset
uspto-grants-1985_09
Patent number
US04540583

Reaction notes

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