1-(1-Azido-1-methylethyl)-3-methoxybenzene → 2-(3-Methoxyphenyl)-2-propanamine

HRID 1373254Notes

Reaction equation

HRID 1373254 reaction equation
[N:1]([C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)([CH3:6])[CH3:5])=[N+]=[N-]>[Ni].C(O)C>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([C:4]([NH2:1])([CH3:5])[CH3:6])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 178157801-(1-Azido-1-methylethyl)-3-methoxybenzene

Product 1

HCID 139113102-(3-Methoxyphenyl)-2-propanamineYield 60.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(1-azido-1-methylethyl)-3-methoxybenzene (34.1 g, 178 mmols), Raney nickel (100 g) and ethanol (300 ml) was stirred at room temperature for 24 hours. The catalyst was removed through decantation, and the resulting supernatant was concentrated under reduced pressure. 1 N hydrochloric acid was added to the residue, which was then washed with diethyl ether. After neutralized, the aqueous layer was made alkaline with sodium hydroxide added thereto, and extracted with ethyl acetate. The extract was washed with brine, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure to give an oil of 1-(3-methoxyphenyl)-1-methylethylamine (17.9 g, 60%).

Workup

  1. customThe catalyst was removed through decantation
  2. concentrationthe resulting supernatant was concentrated under reduced pressure
  3. addition1 N hydrochloric acid was added to the residue, which
  4. washwas then washed with diethyl ether
  5. additionadded
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried with anhydrous magnesium sulfate
  9. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-20bd26b3f2fb401e8793e7ef3436782c
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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