Carbamate → Benzenemethanamine, N-methyl-4-(trifluoromethyl)-

A mixture of 4-(trifluoromethyl)benzylamine (1.0 mL, 7.02 mmol) and di-tert-butyl carbonate (1.68 g, 7.72 mmol) in CH2Cl2 (10 mL) was stirred for 1 hour. The reaction mixture was poured into saturated aqueous ammonium chloride solution, extracted with CH2Cl2 and the organic layers were combined, dried over MgSO4 and concentrated in vacuo to give a white crystalline solid. To a solution of the crude carbamate (1.00 g, 3.61 mmol) in THF (20 mL) in a room temperature water bath, was added LiAlH4 (0.69 g, 18.1 mmol) portion-wise over 10 minutes. The reaction was then heated at reflux for 4 hours. The reaction was cooled in ice and quenched by the addition of water (1.6 mL) and NaOH (2N, 1.3 mL). The grey slurry was filtered and washed with MeOH. The MeOH was removed in vacuo and the crude product taken up in CH2Cl2 and dried over MgSO4 and concentrated in vacuo. Purification by flash column chromatography eluting with 5-10% MeOH in CH2Cl2 plus 1% NH3 solution (2N in MeOH) afforded the title compound.

1. extractionextracted with CH2Cl2
2. dry with materialdried over MgSO4
3. concentrationconcentrated in vacuo
4. customto give a white crystalline solid
5. temperatureThe reaction was then heated
6. temperatureat reflux for 4 hours
7. temperatureThe reaction was cooled in ice
8. customquenched by the addition of water (1.6 mL) and NaOH (2N, 1.3 mL)
9. filtrationThe grey slurry was filtered
10. washwashed with MeOH
11. customThe MeOH was removed in vacuo
12. dry with materialdried over MgSO4
13. concentrationconcentrated in vacuo
14. customPurification by flash column chromatography
15. washeluting with 5-10% MeOH in CH2Cl2 plus 1% NH3 solution (2N in MeOH)

ORD-Eintrag

ord-0fd7b82f0ea3401aac99be59d275d7d7

Quelldatensatz

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07285563B2