tert-Butyl 1-(2,2,2-trifluoroethyl)piperidin-4-ylcarbamate → 1-(2,2,2-Trifluoroethyl)piperidin-4-amine

HRID 1280571Notes

Reaction equation

HRID 1280571 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:10][CH2:9]1)(C)(C)C>O1CCOCC1>[F:18][C:15]([F:16])([F:17])[CH2:14][N:11]1[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 22562166tert-Butyl 1-(2,2,2-trifluoroethyl)piperidin-4-ylcarbamate

Product 1

HCID 162287221-(2,2,2-Trifluoroethyl)piperidin-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[1-(2,2,2-Trifluoroethyl)piperidin-4-yl]-carbamic acid tert-butyl ester was then taken up in dioxane (80 mL) and hydrogen chloride gas was bubbled through the solution for 10 minutes. The reaction vessel was capped tightly and stirred for 1.5 hours. The solvent was removed under reduced pressure at 40° C. The residue was taken up in 42 mL of 0.5M sodium methoxide in methanol, stirred at room temperature for 3 hours, and filtered. The filtrate was concentrated, taken up in ethyl acetate, filtered, and concentrated to give 1.0 g of 1-(2,2,2-trifluoroethyl)piperidin-4-ylamine as a dark colored oil, (M+H)+=183.

Workup

  1. customhydrogen chloride gas was bubbled through the solution for 10 minutes
  2. customThe reaction vessel was capped tightly
  3. customThe solvent was removed under reduced pressure at 40° C
  4. stirringstirred at room temperature for 3 hours
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e15b0496bb37449fa91b82ed8f7a3f58
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

Loading…