Phenethyl bromide → 1-Benzothiophene-2-carboxamide

HRID 1742181Notes

Reaction equation

HRID 1742181 reaction equation
NCC[NH:4][C:5]([C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1OC)=[O:6].C(Br)CC1C=CC=CC=1>C(N(CC)CC)C>[S:11]1[C:7]([C:5]([NH2:4])=[O:6])=[CH:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]1=2

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 19008832HCID 19008832, compound

Product 1

HCID 2370731-Benzothiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

N-(2-Aminoethyl)-3-methoxybenzo[b]thiophene-2-carboxamide (1.56 g) was dissolved in dimethyl fomamide (50 ml) and triethylamine (0.63 g) added. To this stirred solution was added phenethylbromide (1.27 g) and left overnight at ambient temperature. Ice-water was added, and the product extracted with ethyl acetate (3×50 ml). Organic fractions were collected, washed with water (4×50 ml),dried, filtered to yield, after removing the solvent, a clear oil. Flash chromatography eluting with 5% methanol-dichloromethane gave 3-methoxy-N-<2-[N- (2-phenylethyl)amino]ethyl>-benzo[b]thiophene-2-carboxamide which was converted to its hydrochloride.

Workup

  1. additionadded
  2. extractionthe product extracted with ethyl acetate (3×50 ml)
  3. customOrganic fractions were collected
  4. washwashed with water (4×50 ml)
  5. filtrationfiltered
  6. customto yield
  7. customafter removing the solvent
  8. washFlash chromatography eluting with 5% methanol-dichloromethane

Sources & evidence

ORD record
ord-a7ad9fd79d434404a9b651f9a1aef5b7
Source dataset
uspto-grants-1994_08
Patent number
US05338735

Reaction notes

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