Sodium Hydroxide → Benzo(b)thiophene-3-ethylamine, hydrochloride

HRID 501209

Reaction equation

HRID 501209 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-:7].[Al+3].[Cl-].[Cl-].[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([CH2:20][C:21]#[N:22])=[CH:12]1.[OH-].[Na+]>CCOCC>[ClH:7].[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([CH2:20][CH2:21][NH2:22])=[CH:12]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 76681Benzo[b]thiophene-3-acetonitrileHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 209554Benzo(b)thiophene-3-ethylamine, hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a slurry of lithium aluminium hydride (0.6 g, 15.16 mmol) in ether (25 mL) was added, under N2, a slurry of aluminium chloride (2.1 g, 15.1 mmol) in dry ether. After 5 min, a solution of 1-benzothien-3-ylacetonitrile (2.5, 14.4 mmol) in ether (25 mL) was slowly added over 10 min. Upon completion of the addition, the resulting reaction mixture was refluxed for 18 h, cooled and neutralized with 6N NaOH and extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield a syrup. 2-(1-Benzothien-3-yl)ethanamine hydrochloride was obtained by treating the syrup with a solution of methanolic HCl (1.5 g, 50%); 1H NMR (200 MHz, CDCl3): δ 1.43 (s, 2H), 3.00 (m, 4H), 7.11 (s, 1H), 7.36 (m, 2H), 7.72-7.86 (m, 2H).

Workup

  1. additionUpon completion of the addition
  2. customthe resulting reaction mixture
  3. temperaturewas refluxed for 18 h
  4. temperaturecooled
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield a syrup

Sources & evidence

ORD record
ord-5508ba5145d74cb2ac34fa6bab632692
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Linked notes

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