Trifluoroacetic acid → 1-(4-(2-Methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethanamine

HRID 1874636Notes

Reaction equation

HRID 1874636 reaction equation
[CH3:1][CH:2]([CH2:28][CH2:29][CH3:30])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:20]C(=O)OC(C)(C)C)[CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:7][CH:6]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][CH:2]([CH2:28][CH2:29][CH3:30])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH2:20])[CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67430949t-Butyl (1R)-1-(4-(2-methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethylcarbamate

Product 1

HCID 584664091-(4-(2-Methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethanamineYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl (1R)-1-(4-(2-methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethylcarbamate (87 mg, 0.207 mmol) in dichloromethane (1 mL) at 0° C. was added trifluoroacetic acid (0.25 mL, 3.24 mmol). The cooling bath was removed and the mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated and the product was purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA). The organic solvent was removed on the rotovapor and the aqueous mixture was frozen and placed on the lyophilizer to afford 1-(4-(2-methylpentyloxy)phenyl)-2-(4-methylpiperazin-1-yl)ethanamine.3TFA (85.9 mg, 63% yield, 2 steps) as a colorless amorphous semi-solid: 1H NMR (400 MHz, DMSO-d6) δ 9.84 (br. s., 1H), 8.21 (br. s., 3H), 7.38 (d, J=8.6 Hz, 2H), 6.99 (d, J=8.6 Hz, 2H), 4.41 (dt, J=9.5, 4.7 Hz, 1H), 3.83 (dd, J=9.3, 5.8 Hz, 1H), 3.75 (dd, J=9.3, 6.5 Hz, 1H), 3.41 (d, J=11.8 Hz, 2H), 3.13 (d, J=12.6 Hz, 1H), 2.94-3.07 (m, 3H), 2.92 (d, J=13.3 Hz, 1H), 2.72-2.84 (m, 4H), 2.58 (dd, J=13.5, 4.7 Hz, 1H), 2.35 (t, J=11.1 Hz, 1H), 1.87 (dq, J=12.5, 6.3 Hz, 1H), 1.23-1.48 (m, 3H), 1.13-1.22 (m, 1H), 0.96 (d, J=6.8 Hz, 3H), 0.88 (t, J=7.1 Hz, 3 H); LRMS (ESI) m/e 320.3 [(M+H)+, calcd for C19H34N3O 320.3].

Workup

  1. customThe cooling bath was removed
  2. concentrationThe reaction mixture was concentrated
  3. customthe product was purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA)
  4. customThe organic solvent was removed on the rotovapor
  5. temperaturethe aqueous mixture was frozen

Sources & evidence

ORD record
ord-980438eca71d4292bf4b8bb05a7f03db
Source dataset
uspto-grants-2012_11
Patent number
US08304577B2

Reaction notes

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