Triphenylphosphine → 1-(3-Phenylbenzo[b]thiophen-2-yl)ethanamine

HRID 242853Notes

Reaction equation

HRID 242853 reaction equation
[N:1]([CH:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:5])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[C:15]1([C:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:6]=2[CH:4]([NH2:1])[CH3:5])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 11776Triphenylphosphine2×HCID 866688692-(1-Azidoethyl)-3-phenylbenzo[b]thiophene

Product 1

HCID 584591441-(3-Phenylbenzo[b]thiophen-2-yl)ethanamineYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(1-Azidoethyl)-3-phenylbenzo[b]thiophene (211 mg, 0.756 mmol) was dissolved in a mixture THF (4 mL) and water (0.27 mL) and triphenylphosphine (237 mg, 0.91 mmol) was added. The mixture was stirred at RT for 1 h and then additional triphenylphosphine (237 mg) was added. Stirring was continued for 1 h and the crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% MeOH in DCM) affording 1-(3-phenylbenzo[b]thiophen-2-yl)ethanamine as a white solid (160 mg, 83%). 1H NMR (CDCl3, 400 MHz): δ 7.84 (1H, dd, J=7.63, 1.55 Hz), 7.52-7.27 (8H, m), 4.56-4.44 (1H, br), 1.76 (2H, s), 1.47 (3H, d, J=6.21 Hz).

Workup

  1. additionwas added
  2. stirringStirring
  3. waitwas continued for 1 h
  4. customthe crude reaction mixture
  5. washwas washed with MeOH
  6. washthe product eluted with 2M NH3/MeOH
  7. additionThe product containing fractions
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-8% MeOH in DCM)

Sources & evidence

ORD record
ord-64382c79cc614f0a8e8cee1a0ef465e4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…