Hydrochloric Acid → HCID 12529148, compound

HRID 1287674Notes

Reaction equation

HRID 1287674 reaction equation
[CH3:1][N:2]([CH2:11][CH2:12][O:13][C:14](=[O:19])[CH2:15][C:16]([CH3:18])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.[CH3:20][O:21][C:22](=[O:27])/[CH:23]=[C:24](\[NH2:26])/[CH3:25].[F:28][C:29]([F:39])([F:38])[C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=O.[ClH:40]>CC(C)=O.C(O)C.C(O)(C)C>[ClH:40].[CH3:1][N:2]([CH2:11][CH2:12][O:13][C:14]([C:15]1[CH:33]([C:32]2[CH:35]=[CH:36][CH:37]=[C:30]([C:29]([F:28])([F:38])[F:39])[CH:31]=2)[C:23]([C:22]([O:21][CH3:20])=[O:27])=[C:24]([CH3:25])[NH:26][C:16]=1[CH3:18])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 679903-(Trifluoromethyl)benzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 12529176HCID 12529176, compound

Product 1

HCID 12529148HCID 12529148, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

In 3 ml. of isopropyl alcohol were dissolved 1.07 g. of acetoacetic acid β-(N-methyl-N-p-methylbenzylamino)ethyl ester, 0.466 g, of β-aminocrotonic acid methyl ester, and 0.705 g. of m-trifluoromethyl benzaldehyde and the solution was refluxed for 6 hours. The reaction mixture was concentrated, subjected to a silica gel column chromatography (diameter 4 cm, height 15 cm.), and then the effluents containing the aimed product obtained were collected and concentrated. The residue thus obtained was dissolved in acetone and after adjusting the solution to pH 1-2 with an ethanol solution saturated with hydrogen chloride, the solution was concentrated. Then, by crystallizing the residue formed with acetone, 0.8 g. of 2,6-dimethyl-4-(3'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester 5-β-(N-methyl-N-p-methylbenzylamino)ethyl ester hydrochloride was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe effluents containing the aimed product
  3. customobtained
  4. customwere collected
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. concentrationthe solution was concentrated
  8. customThen, by crystallizing the residue
  9. customformed with acetone, 0.8 g

Sources & evidence

ORD record
ord-596f14ed29b544a3bdcc804dc5a38370
Source dataset
uspto-grants-1976_10
Patent number
US03985758

Reaction notes

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