Trifluoroacetic acid → 1-Ethyl-N-methyl-4-piperidinamine

HRID 60246Notes

Reaction equation

HRID 60246 reaction equation
C(O[C:6](=O)[N:7]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH3:16])[CH2:11][CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH2:15]([N:12]1[CH2:13][CH2:14][CH:9]([NH:7][CH3:6])[CH2:10][CH2:11]1)[CH3:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58365208HCID 58365208, compound

Product 1

HCID 167704711-Ethyl-N-methyl-4-piperidinamineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-ethylpiperidin-4-yl)-methylcarbamic acid tert-butyl ester (1.65 g, 6.8 mmol) in dichloromethane (15 mL) was added TFA (5 mL). After 1 hour at ambient temperature the reaction mixture was concentrated in-vacuo and the residue loaded onto a 70 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 an orange oil (900 mg, 94%). 1H NMR (300 MHz, CD3OD): 2.95 (d, J=11.6 Hz, 2H), 2.48-2.36 (m, 3H), 2.35 (s, 3H), 1.96-1.95 (m, 4H), 1.40-1.38 (m, 2H), 1.09 (t, J=7.2 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-81e769a96e9c46eb99842abda97f47df
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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