Hydrazine hydrate (1:1) → 1-(3-Phenylbenzo[b]thiophen-2-yl)ethanamine

HRID 2036598Notes

Reaction equation

[C:1]1([C:7]2[C:8]3[CH:28]=[CH:27][CH:26]=[CH:25][C:9]=3[S:10][C:11]=2[CH:12]([N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>CCO>[C:1]1([C:7]2[C:8]3[CH:28]=[CH:27][CH:26]=[CH:25][C:9]=3[S:10][C:11]=2[CH:12]([NH2:14])[CH3:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-(1-(3-phenylbenzo[b]thiophen-2-yl)ethyl)isoindoline-1,3-dione (170 mg, 0.443 mmol) and hydrazine, monohydrate (0.215 mL, 4.43 mmol) in EtOH (5 mL) was heated to 50° C. overnight. After 18 h, a precipitate had developed. The precipitate was removed by filtration, rinsed with EtOH, and concentrated under reduced pressure. The concentrate was dissolved in DCM, adsorbed onto silica gel and purified by column chromatography using 10% of MeOH in DCM as eluent to give 1-(3-phenylbenzo[b]thiophen-2-yl)ethanamine as a colorless, crystalline solid: 1H NMR (400 MHz, CDCl3) δ 1.51 (d, J=6.5 Hz, 3H), 1.74 (br. s., 2H), 4.55 (q, J=6.5 Hz, 1H), 7.30-7.38 (m, 2H), 7.41-7.57 (m, 6H), 7.87-7.91 (m, 1H); LC-MS (ESI)] m/z 237.1 [M-16]−.

Workup

customThe precipitate was removed by filtration
washrinsed with EtOH
concentrationconcentrated under reduced pressure
dissolutionThe concentrate was dissolved in DCM
custompurified by column chromatography

Sources & evidence

ORD record: ord-b937be761e72487c8ac984a579cbe55f
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575183B2

Reaction notes

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