Formaldehyde → HCID 13247586, compound

Temperature

80 °C

To a solution of 2-phenylpropan-2-amine (1 eq.) in benzene (0.25 M) was added formaldehyde (37% w/w aqueous solution, 2 eq.). The vessel attached a Dean-Stark apparatus and heated at 80° C. for 36 h. The reaction mixture was cooled to RT, dried with Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the crude imine. This was then taken up in methanol (1.4 M) and added sodium borohydride (10 eq.). The resulting mixture was stirred at RT for 2 h and then quenched with 1 N aq. HCl. The volatiles were removed in vacuo and the pH of the resulting residue was carefully brought up to ˜12 with 1 N aq. NaOH. The mixture was then extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of column chromatography (SiO2, 2:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a colorless oil.

1. temperatureThe reaction mixture was cooled to RT
2. dry with materialdried with Na2SO4
3. filtrationfiltered
4. customConcentration of the filtrate in vacuo afforded the crude imine
5. customquenched with 1 N aq. HCl
6. customThe volatiles were removed in vacuo
7. extractionThe mixture was then extracted with EtOAc
8. washThe combined organic extracts were washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationthe filtrate concentrated in vacuo
12. customPurification of the crude product
13. customthus obtained by way of column chromatography (SiO2, 2:1 (v/v) Hex:EtOAc→EtOAc)

ORD record

ord-f274e8b8817c491e806f018d7979b877

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2