Hydrochloric Acid → 3-(1-Aminoethyl)-1-(benzyloxycarbonyl)piperidine

To a solution of 3-(1-azidoethyl)-1-(benzyloxycarbonyl)piperidine (1.95 g, 6.76 mmol) in THF (30.6 mL) was added Ph3P (2.66 g, 10.14 mmol) followed by water (3.4 mL). The mixture was placed in an oil bath at 50° C. for 2.5 h. The reaction mixture was cooled and carefully poured into an Erlenmeyer flask containing 1N HCl. The layers were separated, and the aqueous layer was washed once with EtOAc and the organic layer was discarded. The aqueous layer was then neutralized with saturated aqueous NaHCO3 carefully and was extracted with EtOAc (3×30 mL) and the organic extracts discarded. The aqueous layer was made strongly basic (>pH 12) with SN NaOH, then it was extracted with EtOAc (4×50 mL). The combined organic extracts were washed with brine and dried over Na2SO4. The title compound (950 mg) was used in the next step without purification. Partial 1H NMR (500 MHz, CDCl3): δ 7.3 (m, 5H); 5.12 (s, 2H); 4.1 (brm, 2H); 1.25 (br s, 3H).

1. temperatureThe reaction mixture was cooled
2. additioncarefully poured into an Erlenmeyer flask
3. customThe layers were separated
4. washthe aqueous layer was washed once with EtOAc
5. extractionwas extracted with EtOAc (3×30 mL)
6. extractionit was extracted with EtOAc (4×50 mL)
7. washThe combined organic extracts were washed with brine
8. dry with materialdried over Na2SO4
9. customThe title compound (950 mg) was used in the next step without purification

ORD record

ord-900c6a716a67442a89ff56f420cf1561

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06329380B1