Hydrochloric Acid → trans-2-(1H-pyrrol-1-yl)cyclohexanamine hydrogen chloride

Temperature

80 °C

tert-Butyl N-[(1R,2R)-2-aminocyclohexyl]carbamate (1.06 g, 4.93 mmol), sodium acetate (1.70 g, 20.7 mmol) and 2,5-dimethoxytetrahydrofuran (764 μL, 5.91 mmol) were combined in acetic acid (10.6 mL). The reaction mixture was heated at 80° C. for 16 hours. The reaction mixture was then evaporated to dryness and the residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium bicarbonate. The layers were separated, and the organic layer was washed twice with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, and evaporated to dryness to yield a brown solid. This solid was then dissolved in HCl in dioxane (10.3 mL of 4.0 M, 41.1 mmol) and was allowed to stand for 3 hours. The solvent was then removed to yield trans-2-(1H-pyrrol-1-yl)cyclohexanamine hydrogen chloride (989 mg, 99%) as a brown solid. ESI-MS m/z calc. 164.1, found 165.2 (M+1)+; Retention time: 0.27 minutes (4 min run).

1. customThe reaction mixture was then evaporated to dryness
2. customthe residue was partitioned between ethyl acetate
3. customThe layers were separated
4. washthe organic layer was washed twice with a saturated aqueous solution of sodium chloride
5. dry with materialdried over sodium sulfate
6. customevaporated to dryness
7. customto yield a brown solid
8. customThe solvent was then removed

ORD record

ord-1927ccd022544618a642fdfb6ad742ff

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916565B2