3-Nitrobenzaldehyde → HCID 136364587, compound

HRID 2073607Notes

Reaction equation

HRID 2073607 reaction equation
[C:1]([C:4](=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=1)[C:5]([O:7][CH:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:6])(=O)[CH3:2].[N+](C1C=C(C=CC=1)C=O)([O-])=O.C(OC(C1C=CC=CC=1)CN1CCCCC1)(=O)CC(C)=O.[NH2:64][C:65]1[CH:69]=[CH:68][NH:67][N:66]=1>C(O)C>[CH3:2][C:1]1[NH:64][C:65]2[N:66]([N:67]=[CH:68][CH:69]=2)[CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:4]=1[C:5]([O:7][CH:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:6]

Participants

6

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 13909610HCID 13909610, compoundHCID 53864317HCID 53864317, compoundHCID 178418806HCID 178418806, compound

Product 1

HCID 136364587HCID 136364587, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To 1-phenyl-2-piperidinoethyl α-acetyl-3-nitrocinnamate prepared from 7.5 g of 3-nitrobenzaldehyde and 14.5 g of 1-phenyl-2-piperidinoethyl acetoacetate is added a solution of 4.2 g of 3-aminopyrazole in ethanol, and then stirred at 50° C. for 3 hours. The mixture is concentrated at reduced pressure, and the residue is purified by column chromatography on silica gel with chloroform-ethyl acetate-ethanol eluents to give two forms of diastereromers. The initally eluated solution is concentrated and the residue is recrystallized from ethanol to give one form (α-form) of diastereomer of 1-phenyl-2-piperidinoethyl 5-methyl-7-(3-nitrophenyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate, melting at 92°-93° C. Then, the subsequently eluated solution is concentrated and the residue is recrystallized from ethanol to give the other form (β-form) of diastereomer of 1-phenyl-2-piperidinoethyl 5-methyl-7-(3-nitrophenyl)-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate, melting at 191°-192° C.

Workup

  1. concentrationThe mixture is concentrated at reduced pressure
  2. customthe residue is purified by column chromatography on silica gel with chloroform-ethyl acetate-ethanol eluents
  3. customto give two forms of diastereromers
  4. concentrationThe initally eluated solution is concentrated
  5. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-1bb416d972e94ad4818ba658db4c06f7
Source dataset
uspto-grants-1990_04
Patent number
US04918074

Reaction notes

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