Hydrochloric Acid → Benzeneethanamine, 3-methoxy-beta-methyl-, (+)- (9CI)

HRID 1710887Notes

Reaction equation

HRID 1710887 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH3:12])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH3:12])[CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1361587025310-30-9HCID 21226445Aluminium lithium hydride2×

Product 1

HCID 202627Benzeneethanamine, 3-methoxy-beta-methyl-, (+)- (9CI)Yield 55,758.301%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)propanenitrile (1.33 g, 8.26 mmol) in THF (10 mL) at room temperature was added lithium aluminum hydride (9.1 mL, 1M in THF, 9.1 mmol). The reaction was stirred overnight. More lithium aluminum hydride (0.5 mL) was added and the reaction was refluxed for 4 h. 1 N HCl was added carefully to quench the reaction. It was diluted with ether, washed with H2O. Aqueous layer was treated with NaOH and extracted with CH2Cl2. CH2Cl2 layer was washed with saturated NaCl, dried and concentrated to give 2-(3-methoxyphenyl)-propan-1-amine (761 g, 56% yield) as a pale yellow oil. HPLC retention time (Method C)=1.59 min. LC/MS (ESI) (M+H)+=166.07. 1H NMR (CDCl3, 400 MHz) δ ppm 1.24 (d, J=6.85 Hz, 3H), 2.65-2.77 (m, 1H), 2.85 (d, J=8 Hz, 2H), 3.80 (s, 3H), 6.71-6.84 (m, 3H), 7.20-7.26 (m, 1H).

Workup

  1. temperaturethe reaction was refluxed for 4 h
  2. customto quench
  3. customthe reaction
  4. washwashed with H2O
  5. additionAqueous layer was treated with NaOH
  6. extractionextracted with CH2Cl2
  7. washCH2Cl2 layer was washed with saturated NaCl
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e088a1ca12c14bae8cb0a8e06b3932ce
Source dataset
uspto-grants-2010_09
Patent number
US07790745B2

Reaction notes

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