Ethyl Acetate → 1-[4-(Trifluoromethyl)phenyl]propan-2-amine

HRID 1843934Notes

Reaction equation

HRID 1843934 reaction equation
[N+:1]([C:4]([CH3:16])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)([O-])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OC(=O)C)C>C1COCC1.CCCCCC>[CH3:16][CH:4]([NH2:1])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 66801851HCID 66801851, compound

Product 1

HCID 1215021-[4-(Trifluoromethyl)phenyl]propan-2-amineYield 99.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

1-(2-Nitro-propenyl)-4-trifluoromethyl-benzene (I-43a: 2.85 g, 12.33 mmol) was reacted with LiAlH4 (1.87 g, 49.31 mmol) in dry THF (40 mL). The resulting mixture was refluxed for 5 hours at 70° C. The reaction was monitored by TLC (20% ethylacetate in hexane). The reaction mass was cooled to 0° C., quenched with 10% NaOH solution (2 mL) and stirred for 20 minutes. The precipitated solid was filtered, washed with DCM and concentrated under reduced pressure to afford 2.5 g of the crude product which was used for the next step without further purification. LCMS: m/z=204.1 (M+1)

Workup

  1. temperatureThe reaction mass was cooled to 0° C.
  2. customquenched with 10% NaOH solution (2 mL)
  3. filtrationThe precipitated solid was filtered
  4. washwashed with DCM
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d22a5849050b49969abf17bf24d9eec7
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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