Sodium cyanoborohydride → 1-(4-Iodophenyl)butan-2-amine

HRID 76152Notes

Reaction equation

HRID 76152 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH2:10][CH3:11])=[CH:4][CH:3]=1.[BH3-]C#[N:15].[Na+]>CC(O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH2:15])[CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 594654791-(4-Iodophenyl)butan-2-one

Product 1

HCID 654787241-(4-Iodophenyl)butan-2-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

5.95 g (21.7 mmol) 1-(4-iodophenyl)-butane-2-one (I39) are added to 150 mL 2-propanol and transferred into an autoclav. 25.1 g (326 mmol) NH4OAc and 4.09 g (65.1 mmol) NaCNBH3 are added and the mixture is stirred at 90° C. over night. The reaction is quenched by the addition of sat. aq. NaHCO3 solution and extracted with EtOAc (3×). The combined organic layers are washed with brine, dried with Na2SO4 and the solvent is removed in vacuo. The compound is used without further purification.

Workup

  1. customThe reaction is quenched by the addition of sat. aq. NaHCO3 solution
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried with Na2SO4
  5. customthe solvent is removed in vacuo
  6. customThe compound is used without further purification

Sources & evidence

ORD record
ord-47e8aff04b724365b6255ef04f73b62f
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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