Methanol → HCID 20391032, compound

HRID 426534Notes

Reaction equation

HRID 426534 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:23]=[CH:22][C:21]3[C:20]4[C:15](=[CH:16][C:17]([O:24][CH2:25][CH2:26][CH2:27][N:28]5[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]5)=[CH:18][CH:19]=4)[C:14](=O)[C:13]=3[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH2:37])=[N-].CCOCC.[CH3:43][OH:44]>>[CH3:43][O:44][C:14]1[C:15]2[C:20]([C:21]3[CH:22]=[CH:23][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:12][C:13]=3[CH:37]=1)=[CH:19][CH:18]=[C:17]([O:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH:16]=2

Participants

5

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 20391042HCID 20391042, compound

Product 1

HCID 20391032HCID 20391032, compound

Procedure

A solution of 4.7 g (0.01 mole) of 2,7-bis(3-piperidinopropoxy)fluoren-9-one in methanol is stirred and treated with approximately 0.085 mole of diazomethane by co-distillation with ether into the reaction mixture at a temperature of -15° to -31° C. The reaction mixture is allowed to warm slowly to room temperature overnight. The volatile materials are removed on the steam bath in vacuo and the residue triturated with pentane to induce crystallization. The resulting solid is dissolved in a mixture of pentane and ether, washed several times with a dilute solution of sodium hydroxide, washed with water, dried over anhydrous sodium sulfate, treated with charcoal, filtered and most of the volatile solvents removed from the filtrate. The residue is recrystallized from pentane and again from a methanol-water mixture to yield the desired 9-methoxy-2,7-bis(3-piperidinopropoxy)phenanthrene: m.p. 118.5°-9.5° C., λmaxMeOH 259, and E1cm1% 1430.

Workup

  1. customThe volatile materials are removed on the steam bath in vacuo
  2. customthe residue triturated with pentane
  3. customcrystallization
  4. dissolutionThe resulting solid is dissolved in a mixture of pentane and ether
  5. washwashed several times with a dilute solution of sodium hydroxide
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. additiontreated with charcoal
  9. filtrationfiltered and most of the volatile solvents
  10. customremoved from the filtrate
  11. customThe residue is recrystallized from pentane and again from a methanol-water mixture

Sources & evidence

ORD record
ord-a9e4eee009454d09827084647c08093e
Source dataset
uspto-grants-1979_10
Patent number
US04169897

Reaction notes

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