Hydrochloric Acid → 1-(4-Iodophenyl)cyclopropanamine

Titanium(IV) isopropoxide (7.1 mL) was added to a diethyl ether (0.14 L) solution of 4-iodobenzonitrile (5.0 g) and, with the internal temperature being kept at −60° C. or lower, a THF solution (53 mL) of 0.90 mol/L ethylmagnesium bromide was added dropwise. After the mixture was stirred for 1 hour at room temperature, boron trifluoride diethyl etherate (5.4 mL) was added, and the mixture was stirred for 3 hours at room temperature. Upon addition of 1.0 mol/L hydrochloric acid (65 mL), the aqueous layer was washed with diethyl ether. A 1.0 mol/L sodium hydroxide aqueous solution was added to the washed aqueous layer to bring it to pH 9. The precipitate was filtered out using Celite, and the filtrate was extracted with ethyl acetate. The extract was dried over magnesium sulfate, whereafter the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=50/50→1/99) to obtain 1-(4-iodophenyl)cyclopropylamine (light yellow solid) (1.3 g, 23%).

1. custombeing kept at −60° C.
2. stirringthe mixture was stirred for 3 hours at room temperature
3. washthe aqueous layer was washed with diethyl ether
4. additionA 1.0 mol/L sodium hydroxide aqueous solution was added to the washed aqueous layer
5. filtrationThe precipitate was filtered out
6. extractionthe filtrate was extracted with ethyl acetate
7. dry with materialThe extract was dried over magnesium sulfate, whereafter the desiccant
8. filtrationwas filtered out
9. distillationthe solvent was distilled off under reduced pressure
10. customThe resulting residue was purified by OH type silica gel chromatography (gradient elution with hexane/ethyl acetate=50/50→1/99)

ORD record

ord-0c03ca21360b48c5972d652cf98f1e76

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073821B2