HCID 14835770, compound → HCID 14835771, compound

HRID 1709261Notes

Reaction equation

HRID 1709261 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:13][CH2:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[CH:9]([N:18]3[CH2:23][CH2:22][N:21]([CH2:24]/[CH:25]=[CH:26]/[C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([NH:33]C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:28]=4)[CH2:20][CH2:19]3)[C:8]=2[CH:53]=1)([O-:3])=[O:2]>C(O)(=O)C.CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:13][CH2:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[CH:9]([N:18]3[CH2:19][CH2:20][N:21]([CH2:24]/[CH:25]=[CH:26]/[C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([NH2:33])[CH:28]=4)[CH2:22][CH2:23]3)[C:8]=2[CH:53]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 14835770HCID 14835770, compound

Product 1

HCID 14835771HCID 14835771, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

7.0 g of 3-nitro-5-[4-{(E)-3-(3-triphenylmethylaminophenyl)allyl}piperazin-1-yl]-10,11-dihydro-5H-dibenzo[a,d]cycloheptene was dissolved in 20 ml of acetic acid and 20 ml of methanol. The solution was stirred for 2 hours at 40° C. The solvent was removed by distillation under reduced pressure. The residue was dissolved in 100 ml of ethyl acetate. The solution was washed with a saturated aqueous sodium hydrogen-carbonate solution, water and a saturated aqueous sodium chloride solution in this order and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: chloroform/ethanol=50/1) to obtain 3.77 g of light yellow solid 3-nitro-5-[4-{(E)-3-(3-aminophenyl)allyl}-piperazin-1-yl]-10,11-dihydro-5H-dibenzo[a,d]cycloheptene.

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. dissolutionThe residue was dissolved in 100 ml of ethyl acetate
  3. washThe solution was washed with a saturated aqueous sodium hydrogen-carbonate solution, water
  4. dry with materiala saturated aqueous sodium chloride solution in this order and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by a column chromatography (eluant: chloroform/ethanol=50/1)

Sources & evidence

ORD record
ord-6dab5968fcea45678e5f428292347f5d
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

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