Water → Benzo[b]thiophen-6-ylmethanamine

HRID 2041231Notes

Reaction equation

HRID 2041231 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]1[CH:11]=[CH:10][C:9]2[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][C:8]1=2.O.[OH-].[Na+]>C1COCC1>[NH2:17][CH2:16][C:14]1[CH:13]=[CH:12][C:9]2[CH:10]=[CH:11][S:7][C:8]=2[CH:15]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21816574Benzo[b]thiophene-6-carbonitrile

Product 1

HCID 54322319Benzo[b]thiophen-6-ylmethanamineYield 93.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Add 1M lithium aluminum hydride in THF (7.3 mL) to benzo[b]thiophene-6-carbonitrile (0.6 g, 3.6 mmol) at 0° C. in THF (36 mL). After 15 h at ambient temperature, cool to 0° C. and add sequentially water (1.82 mL), 2N aqueous NaOH (1.82 mL) and water (2.60 mL). Filter the solid 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 in vacuo to give the title compound (0.55 g, 92%).

Workup

  1. filtrationFilter the solid
  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 in vacuo

Sources & evidence

ORD record
ord-541f4041e1e84a6ba8058a2d52d89ac1
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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