2-(Oxiran-2-ylmethoxy)benzonitrile → HCID 70393940, compound

HRID 620079Notes

Reaction equation

HRID 620079 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=2)[C:7]([C:13]([O:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH2:27])=[CH:21][CH:20]=2)=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4].[O:37]1[CH2:49][CH:38]1[CH2:39][O:40][C:41]1[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=1[C:43]#[N:44]>C(O)(C)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-:36])=[O:35])[CH:29]=2)[C:7]([C:13]([O:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][NH:27][CH2:49][CH:38]([OH:37])[CH2:39][O:40][C:41]3[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=3[C:43]#[N:44])=[CH:23][CH:24]=2)=[O:14])=[C:8]([CH3:12])[NH:9][C:10]=1[CH3:11])=[O:4]

Participants

4

Reactant 2

HCID 126196712-(Oxiran-2-ylmethoxy)benzonitrileHCID 70393862HCID 70393862, compound

Product 1

HCID 70393940HCID 70393940, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4.1 g (8.3 mmol) of 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{2-[p-(2-aminoethyl)-phenoxy]-ethyl}-ester 5-methyl ester and 1.6 g of 2-(2,3-epoxypropoxy)-benzonitrile in 20 ml of isopropanol is heated under reflux for 2 hours and then concentrated to dryness by evaporation under reduced pressure. The residue is dissolved in 20 ml of 1N methanesulphonic acid and extracted with 40 ml of ethyl acetate. The aqueous phase is separated off and rendered alkaline with 2N sodium hydroxide solution. The crude product obtained by extraction with ethyl acetate is "flash" chromatographed over silica gel using toluene/isopropanol/concentrated ammonia (170:30:3) as eluant. 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-pyridine-3,5-dicarboxylic acid 3-{{{2-{{p-{2-[3-(o-cyanophenoxy)-2-hydroxypropylamino]-ethyl}-phenoxy}}-ethyl}}}-ester 5-methyl ester is obtained in the form of an amorphous foam.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrated to dryness by evaporation under reduced pressure
  4. dissolutionThe residue is dissolved in 20 ml of 1N methanesulphonic acid
  5. extractionextracted with 40 ml of ethyl acetate
  6. customThe aqueous phase is separated off
  7. customThe crude product obtained by extraction with ethyl acetate
  8. customchromatographed over silica gel

Sources & evidence

ORD record
ord-ae6562f6ba03463b898a13677f767bd2
Source dataset
uspto-grants-1989_04
Patent number
US04818766

Reaction notes

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