Water → Benzo[b]thiophen-6-ylmethanamine

HRID 1986190Notes

Reaction equation

HRID 1986190 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][C:8]([CH2:10][NH2:11])=[CH:9][C:2]1=2

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 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

Benzo[b]thiophene-6-carbonitrile (9.70 g, 61.1 mmol) is dissolved in THF (400 mL) and cooled to 0-5° C. Lithium aluminum hydride (183 mL of 1.0 M solution in THF) is added dropwise over 30 minutes and the reaction is stirred for 20 hours while warming to 25° C. The reaction is cooled with an ice bath and water (6.94 mL) is slowly added followed by 15% sodium hydroxide (6.94 mL) and water (20.83 mL). The resulting precipitate is filtered and washed with diethyl ether. The filtrate is concentrated to give the title compound as a colorless oil (8.16 g, 82% yield). ES+(m/z) 164 [M+H].

Workup

  1. temperaturewhile warming to 25° C
  2. temperatureThe reaction is cooled with an ice bath
  3. filtrationThe resulting precipitate is filtered
  4. washwashed with diethyl ether
  5. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-390d32111740437dab9bba2e3f55b663
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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