Hydrochloric Acid → 2-(4-Fluorophenoxy)-2-methylpropan-1-amine

Temperature

65 °C

Into a 1 L-single neck round-bottom flask was added 2-(4-fluorophenoxy)-2-methylpropanoic acid (5.10 g, 0.0257 mol), methylene chloride (66.0 mL, 1.03 mol), oxalyl chloride (3.27 mL, 0.0386 mol) and N,N-dimethylformamide (20 μL, 0.0003 mol). The reaction was stirred until bubbling had stopped. Volatiles were removed and crude product then dissolved in DCM and 15 mL of 7N ammonia in MeOH was added. Volatiles were removed and crude product then dissolved in DCM and 15 mL of 7N ammonia in MeOH was added. Borane-dimethyl sulfide complex (5.7 mL, 0.064 mol) was added to the amide in THF (50 mL, 0.6 mol) at room temperature. The reaction was heated at 65° C. overnight. MeOH was added carefully. 1 N HCl was added and was heated at 65° C. for 2 hours. The reaction was concentrated in vacuo. The solid was dissolved in water and was washed with DCM. The aq. layer was basified with 1 N NaOH. The reaction was extracted with DCM. The reaction was dried with MgSO4 and concentrated in vacuo to afford the title compound.

1. customuntil bubbling
2. customVolatiles were removed
3. dissolutioncrude product then dissolved in DCM
4. addition15 mL of 7N ammonia in MeOH was added
5. customVolatiles were removed
6. dissolutioncrude product then dissolved in DCM
7. addition15 mL of 7N ammonia in MeOH was added
8. temperaturewas heated at 65° C. for 2 hours
9. concentrationThe reaction was concentrated in vacuo
10. dissolutionThe solid was dissolved in water
11. washwas washed with DCM
12. extractionThe reaction was extracted with DCM
13. dry with materialThe reaction was dried with MgSO4
14. concentrationconcentrated in vacuo

ORD record

ord-24787a9f38244f82ad2f67751e3a51e4

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741934B2