Water → 1-(Para-fluorophenyl)-3-(ethylamino)propane

HRID 1592354Notes

Reaction equation

HRID 1592354 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=O)[CH3:13])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH3:13])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 589976581-(Para-fluorophenyl)-3-(acetamido)propane

Product 1

HCID 589976461-(Para-fluorophenyl)-3-(ethylamino)propaneYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product of Step d (1.10 g, 5.63 mmol, 1 eq.) was dissolved in THF at 25° C. under N2 then 1.0M LAH in THF (22.54 mL, 22.50 mmol, 4 eq.) was added dropwise via an addition funnel over 10 minutes. After the addition was complete, refluxed for 1 hour. Worked up by carefully adding water (0.86 mL)(Caution—lots of foaming and gas evolution were observed) dropwise via an addition funnel followed by 1N NaOH (3.42 mL). Stirred 20 minutes then filtered off the solids. The filtrate was stripped to give 0.90 g of a colorless oil as product. MS (ESI) detects (M+H)+=182.

Workup

  1. additionAfter the addition
  2. temperaturerefluxed for 1 hour
  3. filtrationthen filtered off the solids

Sources & evidence

ORD record
ord-4fd2fbf61a714809883e2dfab5297919
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

Loading…