Dimethylamine → 2-[3-[3-(N,N-Dimethylaminomethyl)phenoxy]propyl]-1H-isoindole-1,3(2H)-dione

HRID 1493179Notes

Reaction equation

HRID 1493179 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])=O.[CH3:24][NH:25][CH3:26]>C(O)C.[Pd]>[CH3:24][N:25]([CH2:1][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[CH3:26]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 128106403-(3-(1,3-Dioxoisoindolin-2-yl)propoxy)benzaldehyde

Product 1

HCID 128106112-[3-[3-(N,N-Dimethylaminomethyl)phenoxy]propyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-[3-[3-(Formyl)phenoxy]propyl]-1H-isoindole-1,3(2H) dione (132 g) and 33% ethanolic dimethylamine (300 ml) were hydrogenated at room temperature and atmospheric pressure in ethanol over 10% palladium on charcoal. The catalyst was filtered off and the filtrate evaporated to give the title compound as a yellow oil (142 g). TLC silica (ethyl acetate) Rf 0.35, m.p. (oxalate salt) 204°-207°.

Workup

  1. customwere hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-2fd0fd6ad18d4f8da6d9533d3ecf31a7
Source dataset
uspto-grants-1991_06
Patent number
US05021429

Reaction notes

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