Water → 4-(4-Methylthiophenoxy)benzylamine

To a stirred mixture of potassium phthalimide (3.60 g, 19.4 mM) and dry N,N-dimethylformamide (200 ml) was added dropwise a solution of 4-(4-methylthiophenoxy)benzylbromide (5.00 g, 16.2 mM) in dry N,N-dimethylformamide at room temperature, the mixture was stirred for 5 h at the same temperature. The mixture was poured into water, and the mixture was extracted with toluene. The extract was washed with 5N NaOH, water and brine, dried with magnesium sulfate, and concentrated in vacuo. The residue was diluted with methanol (200 ml), and to the mixture was added dropwise hydrazine monohydrate (1.10 g, 21.1 mM). The mixture was stirred for 6 h under reflux, and this was cooled to the room temperature and concentrated in vacuo. The residue was diluted with chloroform and the mixture was filtered through celite. The filtrate was washed with 5N NaOH(x3) and brine(x2), dried with potassium carbonate, and concentrated in vacuo to give 4-(4-methylthiophenoxy)benzylamine (3.02 g, 76%) as colorless crystals, m.p. 61.8° C.

1. extractionthe mixture was extracted with toluene
2. washThe extract was washed with 5N NaOH, water and brine
3. dry with materialdried with magnesium sulfate
4. concentrationconcentrated in vacuo
5. additionThe residue was diluted with methanol (200 ml)
6. additionto the mixture was added dropwise hydrazine monohydrate (1.10 g, 21.1 mM)
7. stirringThe mixture was stirred for 6 h
8. temperatureunder reflux
9. concentrationconcentrated in vacuo
10. additionThe residue was diluted with chloroform
11. filtrationthe mixture was filtered through celite
12. washThe filtrate was washed with 5N NaOH(x3) and brine(x2)
13. dry with materialdried with potassium carbonate
14. concentrationconcentrated in vacuo

ORD record

ord-504320d8d163486aa1c82c50fa1cb756

Source dataset

uspto-grants-1993_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05206259