2-(4-Benzyloxy-2-methoxymethoxyphenyl)ethylamine → 4-(2-Aminoethyl)-3-methoxymethoxyphenol

HRID 853948Notes

Reaction equation

HRID 853948 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH2:17])=[C:11]([O:18][CH2:19][O:20][CH3:21])[CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[NH2:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]=1[O:18][CH2:19][O:20][CH3:21]

Participants

4

Reactant 1

HCID 178562142-(4-Benzyloxy-2-methoxymethoxyphenyl)ethylamine

Product 1

HCID 178562194-(2-Aminoethyl)-3-methoxymethoxyphenolYield 102.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 18.00 g of 2-(4-benzyloxy-2-methoxymethoxy phenyl)ethylamine, 3.6 g of 10% palladium on carbon (Degussa Inc.: E101 NE/W) and 230 mL of ethanol was stirred under a hydrogen atmosphere at room temperature for 1 hour. After the catalyst was filtered off through a diatomaceous earth, the filtrate was concentrated under reduced pressure to give 12.65 g of 4-(2-aminoethyl)-3-methoxymethoxyphenol as a colorless solid.

Workup

  1. filtrationAfter the catalyst was filtered off through a diatomaceous earth
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b9268d8be3c544318edab3b50895fb70
Source dataset
uspto-grants-2007_08
Patent number
US07256215B2

Reaction notes

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