Heptanal → Ethyl 2-[4-(heptylaminoethyl)phenoxy]-2-methylpropionate

HRID 2258021Notes

Reaction equation

HRID 2258021 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1.[CH:19](=O)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(O)C>[CH2:19]([NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]([CH3:15])([CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:17][CH:18]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 8130HeptanalHCID 19356632Ethyl 2-[4-(2-aminoethyl)-phenoxy]-2-methylpropionate

Product 1

HCID 23192930Ethyl 2-[4-(heptylaminoethyl)phenoxy]-2-methylpropionateYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from step (c) (1.5 g) and heptaldehyde (0.7 g) were mixed together in a observably exothermic reaction and the product dissolved in absolute ethanol (100 ml). Paar hydrogenation for 1.0 hour resulted in a drop in bottle pressure from 49.0 to 42.7 psi. The Pd/C was removed by filtration and the filtrate evaporated in vacuo to give the desired product as a colourless oil (2.1 g).

Workup

  1. customPaar hydrogenation for 1.0 hour resulted in a drop in bottle pressure from 49.0 to 42.7 psi
  2. customThe Pd/C was removed by filtration
  3. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-aee84cb6c5ac42508de0aa21fdec207d
Source dataset
uspto-grants-1997_08
Patent number
US05658944

Reaction notes

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