Ammonia → 1-Benzothiophen-5-ylmethylamine

HRID 2304902Notes

Reaction equation

HRID 2304902 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1.[NH3:12]>CN(C=O)C>[S:7]1[CH:8]=[CH:9][C:5]2[CH:4]=[C:3]([CH2:2][NH2:12])[CH:11]=[CH:10][C:6]1=2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 111604985-(Bromomethyl)benzo[b]thiophene

Product 1

HCID 27954481-Benzothiophen-5-ylmethylamineYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5-bromomethylbenzo[b]thiophene (3.0 g, 13.20 mmol) in DMF (15 ml) was added to a solution of 25% aqueous ammonia (10 ml, 132 mmol) in DMF (10 ml). The reaction mixture was stirred for 4 hours at room temperature. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g), using first ethyl acetate/heptane (1:1;60 ml) and subsequently DCM/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 0.40 g (19%) of ((benzo[b]thiophen-5-yl)methyl)amine.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude product was purified by flash chromatography on silica (40 g)

Sources & evidence

ORD record
ord-cef2d551fc7c4e40b3212a15cd056c4b
Source dataset
uspto-grants-2002_08
Patent number
US06437147B1

Reaction notes

Loading…