3-Nitrobenzaldehyde → HCID 13589488, compound

HRID 2073608Notes

Reaction equation

HRID 2073608 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[NH:66][CH:67]=[CH:68][N:69]=1.S(O)(O)(=O)=O.NC1NC=CN=1.[OH-].[Na+]>C(O)C>[CH3:2][C:1]1[NH:64][C:65]2[N:66]([CH:67]=[CH:68][N: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

8

Reactant 6

HCID 74493-NitrobenzaldehydeHCID 14798Sodium HydroxideHCID 821402-AminoimidazoleHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 13909610HCID 13909610, compoundHCID 53864317HCID 53864317, compound

Product 1

HCID 13589488HCID 13589488, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To the crude 1-phenyl-2-piperidinoethyl α-acetyl-3-nitrocinnamate, which was synthesized by reacting 30 g of 3-nitrobenzaldehyde with 67 g of 1-phenyl-2-piperidinoethyl acetoacetate, is added 500 ml of ethanol solution of 2-aminoimidazole prepared from 26.4 g of 2-aminoimidazole sulfate and sodium hydroxide, and then stirred at 50° C. for 5 hours. After cooling, the precipitated crystals are collected by filtration and recrystallized from ethanol to give 9.7 g of 1-phenyl-2-piperidinoethyl 7-methyl-5-(3-nitrophenyl)-5,8-dihydroimidazo[1,2-a]pyrimidine-6-carboxylate, melting at 205°-206° C. as one diastereomer (α-form). Then, the filtrate is concentrated under reduced pressure, and the residue is purified by column chromatography on silica gel with chloroform-ethyl acetate-ethanol eluents. The crystals thus obtained are recrystallized from a mixture of chloroform and ethanol to give 4.8 g of 1-phenyl-2-piperidinoethyl 7-methyl-5-(3-nitrophenyl)-5,8-dihydroimidazo[1,2-a]pyrimidine-6-carboxylate, melting at 216° -217° C. with decomposition as the other diastereomer (β-form).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated crystals are collected by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5908074aa0b24c49b2dfc7efdae07043
Source dataset
uspto-grants-1990_04
Patent number
US04918074

Reaction notes

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