Trifluoroacetic acid → 1-(Methanesulfonyl)piperidin-4-amine

HRID 538634Notes

Reaction equation

HRID 538634 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:17][S:14]([N:11]1[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25250149tert-Butyl [1-(methanesulfonyl)piperidin-4-yl]carbamate

Product 1

HCID 113558261-(Methanesulfonyl)piperidin-4-amineYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.30 g (22.63 mmol) of (1-methanesulfonyl-piperidin-4-yl)-carbamic acid tert-butyl ester are dissolved in DCM (74 mL) and 17.4 mL (226 mmol) TFA are added. The reaction is stirred at RT for 16 h. The solvent is removed under reduced pressure. The crude product is diluted with diethylether at 40° C., the precipitate is filtered, washed with water and dried. The product is dissolved in MeOH, polymer supported hydrogencarbonate (PL-HCO3 MP Resin, Agilent Technologies) is added and the suspension is stirred for a few minutes. The resin is filtered and the solvent is removed under reduced pressure to afford 4.00 g of 1-methanesulfonyl-piperidin-4-ylamine. Yield: 99%; ESI-MS: 179 [M+H]+; HPLC (Rt): 0.26 min (method E)

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionThe crude product is diluted with diethylether at 40° C.
  3. filtrationthe precipitate is filtered
  4. washwashed with water
  5. customdried
  6. dissolutionThe product is dissolved in MeOH
  7. additionis added
  8. stirringthe suspension is stirred for a few minutes
  9. filtrationThe resin is filtered
  10. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-4ab56925ae694dc98c5d7d3425209120
Source dataset
uspto-grants-2014_10
Patent number
US08865744B1

Reaction notes

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