Water → 4-(Aminomethyl)benzo[b]thiophene

HRID 911341Notes

Reaction equation

HRID 911341 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]1[CH:11]=[CH:10][C:9]2[C:12]([C:16]#[N:17])=[CH:13][CH:14]=[CH:15][C:8]1=2.O.[OH-].[Na+]>C1COCC1>[NH2:17][CH2:16][C:12]1[C:9]2[CH:10]=[CH:11][S:7][C:8]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 218165751-Benzothiophene-4-carbonitrile

Product 1

HCID 533972084-(Aminomethyl)benzo[b]thiopheneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Add lithium aluminum hydride (1M solution in THF, 7.5 mL) to benzo[b]thiophene-4-carbonitrile (prepared as described in WO 0168653) (0.6 g, 3.8 mmol) at 0° C. in THF (38 mL). After 17 h at ambient temperature, cool to 0° C. and add sequentially water (1.89 mL), 2N aqueous NaOH (1.89 mL) and water (2.69 mL). Filter the solids and evaporate the filtrate to obtain the crude amine. Purify by SCX chromatography. Rinse the column with methanol, add a solution of the crude amine in methanol, wash the column with methanol and then elute with 1N ammonia in methanol. Concentrate to give the title compound (0.57 g, 93%). GC-MS m/z: 163 (M+).

Workup

  1. filtrationFilter the solids
  2. customevaporate the filtrate
  3. customto obtain the crude amine
  4. customPurify by SCX chromatography
  5. washRinse the column with methanol
  6. additionadd a solution of the crude amine in methanol
  7. washwash the column with methanol
  8. washelute with 1N ammonia in methanol
  9. concentrationConcentrate

Sources & evidence

ORD record
ord-bf65219f24c0479dbfe318efd2748f58
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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