28446-69-7 → 3-(3-methoxyphenyl)propan-1-amine

HRID 1736500Notes

Reaction equation

HRID 1736500 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[C:11]#[N:12])[CH:6]=[CH:7][CH:8]=1>CCO.C(Cl)(Cl)Cl.O=[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][NH2:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 1

HCID 614917328446-69-7

Product 1

HCID 30298093-(3-methoxyphenyl)propan-1-amineYield 85%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of trans-3-(3-Methoxyphenyl)-2-propenenitrile (27.6 g, 173 mmol) and PtO2 (2.76 g) in 200 mL of EtOH and 30 mL of CHCl3 was shaken in a Parr apparatus under an atmosphere of 50-60 psi H2 overnight at RT. The reaction mixture was filtered through Celite and concentrated in vacuo to provide a brown solid which was then partitioned between CH2Cl2 and 1N NaOH. The organic phase was separated and the aqueous phase was extracted with CH2Cl2 (3×100 mL). The combined organic layers were then dried over MgSO4, filtered and concentrated in vacuo to provide 24.2 g of the desired product as a yellow oil (85% yield). 1H NMR (CDCl3) δ 7.15-7.22 (m, 1H), 6.70-6.80 (m, 3H), 3.80 (s, 3H), 2.72 (t, J=6.0 Hz, 2H), 2.58-2.65 (m, 2H), 1.70-1.85 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customto provide a brown solid which
  4. customwas then partitioned between CH2Cl2 and 1N NaOH
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with CH2Cl2 (3×100 mL)
  7. dry with materialThe combined organic layers were then dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd4043df2acb42009fa95978e5272c4c
Source dataset
uspto-grants-1996_07
Patent number
US05541228

Reaction notes

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