Methanol → Phthalimidoamlodipine

HRID 2242494Notes

Reaction equation

HRID 2242494 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH:4]=[C:5]([C:10]([CH3:12])=O)[C:6]([O:8][CH3:9])=[O:7].[NH2:17]/[C:18](/[CH2:25][O:26][CH2:27][CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39])=[CH:19]\[C:20]([O:22][CH2:23][CH3:24])=[O:21].CO>CC(O)C>[CH3:24][CH2:23][O:22][C:20]([C:19]1[CH:4]([C:3]2[C:2]([Cl:1])=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:10]([CH3:12])[NH:17][C:18]=1[CH2:25][O:26][CH2:27][CH2:28][N:29]1[C:30](=[O:39])[C:31]2[C:32](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]1=[O:34])=[O:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 299600Methyl 2-[(2-chlorophenyl)methylidene]-3-oxobutanoateHCID 11174576HCID 11174576, compound

Product 1

HCID 9871958PhthalimidoamlodipineYield 69.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-(2-chlorobenzyliden)acetoacetate (40.6 g; 169.9 mmol) was condensed with ethyl 3-amino-4-[2-(phthalimido)ethoxy]crotonate (51.5 g; 161.8 mmol) in 2-propanol (160 ml) under reflux for 11 hours. Methanol (103 ml) was added and mixture was cooled to 5/0° C. The solid was filtered off and dried at 40° C. Phthaloyl Amlodipine (60.7 g, purity: 98.6%; 0.86% of impurity HA) was obtained.

Workup

  1. temperatureunder reflux for 11 hours
  2. filtrationThe solid was filtered off
  3. customdried at 40° C

Sources & evidence

ORD record
ord-7c0a0754e20441159ba41fcc575d72d9
Source dataset
uspto-grants-2010_03
Patent number
US07671208B2

Reaction notes

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