Water → 2-(3-Methylthiophen-2-yl)ethan-1-amine

HRID 240827Notes

Reaction equation

HRID 240827 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C:8]#[N:9].[BH4-].[Na+].O>C(O)C.[Ni](Cl)Cl>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][CH2:8][NH2:9]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 18183262HCID 18183262, compound

Product 1

HCID 143617502-(3-Methylthiophen-2-yl)ethan-1-amineYield 50%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 702EthanolSolvent

Procedure

Nickel chloride (0.95 g, 0.73 mmol) was slowly added dropwise to the solution of 2-(3-methylthiophen-2-yl) acetonitrile obtained in step (45-2) (0.10 g 0.73 mmol) in ethanol (3 mL). To a reaction mixture was added portion wise sodium borohydride (0.83 g, 2.19 mmol), and was stirred at room temperature. Water (30 mL) was sequentially added to the mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by flash column chromatography (dichloro methane:methanol=8:2), to obtain the title compound (51 mg, 50%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (dichloro methane:methanol=8:2)

Sources & evidence

ORD record
ord-d6f715dd8fe24723a2cdf1346de7b9d8
Source dataset
uspto-grants-2014_02
Patent number
US08648111B2

Reaction notes

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