diethyl N-benzyl-N-(2,4-dimethoxybenzyl)-amino-malonate → Diethyl {[(2,4-dimethoxyphenyl)methyl]amino}propanedioate

HRID 1903010Notes

Reaction equation

HRID 1903010 reaction equation
C([N:8]([CH:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[O:18][CH3:19])C1C=CC=CC=1>[Pd].C(O)C>[CH3:19][O:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 1

HCID 13422977diethyl N-benzyl-N-(2,4-dimethoxybenzyl)-amino-malonate

Product 1

HCID 13422978Diethyl {[(2,4-dimethoxyphenyl)methyl]amino}propanedioateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

61.7 g. (0.149 moles) of diethyl N-benzyl-N-(2,4-dimethoxybenzyl)-amino-malonate prepared according to Example 7(b) are hydrogenated in the presence of 20 g. of palladium-on-charcoal, in 500 ml. of ethanol, under atmospheric pressure. The catalyst is filtered off and the filtrate is evaporated. 47.1 g. (97%) of diethyl N-(2,4-dimethoxybenzyl)-amino-malonate are obtained. If desired, the product is converted into the corresponding hydrochloride, which melts at 122° to 124° C. (EtOAc).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-b5e06dca7f0343b8b433d9884d6981c2
Source dataset
uspto-grants-1984_03
Patent number
US04435322

Reaction notes

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