Trifluoroacetic acid → 1-(Oxetan-3-YL)piperidin-4-amine

HRID 60242Notes

Reaction equation

HRID 60242 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:17][O:16][CH2:15]2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[O:16]1[CH2:17][CH:14]([N:11]2[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]2)[CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 56604528tert-Butyl 1-(oxetan-3-yl)piperidin-4-yl carbamate

Product 1

HCID 552828551-(Oxetan-3-YL)piperidin-4-amineYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-oxetan-3-yl-piperidin-4-yl)-carbamic acid tert-butyl ester (134 mg, 0.52 mmol) in dichloromethane (2 mL) was added TFA (2 mL). After 15 minutes at ambient temperature the reaction mixture was concentrated in-vacuo and the residue loaded onto a 5 g SCX-2 cartridge which was washed with methanol, then 2N ammonia in methanol. Concentration of the combined basic fractions in-vacuo afforded the title compound as a colourless gum (82 mg, 100%). 1H NMR (400 MHz, CDCl3): 4.63-4.63 (m, 4H), 3.47-3.45 (m, 1H), 2.69-2.68 (m, 3H), 1.90-1.81 (m, 4H), 1.41-1.40 (m, 2H).

Workup

  1. concentrationAfter 15 minutes at ambient temperature the reaction mixture was concentrated in-vacuo
  2. washwas washed with methanol

Sources & evidence

ORD record
ord-7fb686a54cc94986a94f90d6f1e86aa4
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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