Hydrochloric Acid → 1-(3-(3,5-Difluorophenyl)benzo[b]thiophen-2-yl)ethanamine

HRID 2036602Notes

Reaction equation

HRID 2036602 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]3[CH:26]=[CH:25][CH:24]=[CH:23][C:11]=3[S:12][C:13]=2[CH:14]([NH:16]S(C(C)(C)C)=O)[CH3:15])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl>C1COCC1>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[C:10]3[CH:26]=[CH:25][CH:24]=[CH:23][C:11]=3[S:12][C:13]=2[CH:14]([NH2:16])[CH3:15])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58459329N-(1-(3-(3,5-difluorophenyl)-benzo[b]thiophen-2-yl)ethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 584591961-(3-(3,5-Difluorophenyl)benzo[b]thiophen-2-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(1-(3-(3,5-difluorophenyl)benzo[b]thiophen-2-yl)ethyl)-2-methylpropane-2-sulfinamide (392 mg, 0.996 mmol) in THF (7 mL) at rt was added HCl (1.0 mL, 11.85 mmol). The reaction was stirred at ambient temperature for 10 min, after which time LC-MS indicated no starting material remained. The reaction was poured into satd. aq. NaHCO3 and extracted two times with EtOAc. The combined organic extracts were stirred over MgSO4, filtered and concentrated under reduced pressure to give 1-(3-(3,5-difluorophenyl)benzo[b]thiophen-2-yl)ethanamine as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 1.35 (d, J=6.7 Hz, 3H), 1.60 (br. s., 2H), 4.39 (q, J=6.6 Hz, 1H), 6.73-6.86 (m, 3H), 7.19-7.24 (m, 2H), 7.30-7.36 (m, 1H), 7.71-7.77 (m, 1H); LC-MS (ESI)] m/z 273.0 [M+H]+.

Workup

  1. additionThe reaction was poured into satd
  2. extractionaq. NaHCO3 and extracted two times with EtOAc
  3. stirringThe combined organic extracts were stirred over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b1b0306e31e429bbcf4b6ca89f15a7d
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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