Trifluoroacetic acid → 1-[(4-Fluorophenyl)methyl]-5-[2-(methoxymethylamino)ethyl]-2-piperazinone

HRID 1162824Notes

Reaction equation

HRID 1162824 reaction equation
C(OC([N:8]([CH2:17][CH:18]([NH:25][CH2:26][C:27]([O:29]C)=O)[CH2:19][CH2:20][N:21]([O:23][CH3:24])[CH3:22])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:8]2[CH2:17][CH:18]([CH2:19][CH2:20][N:21]([O:23][CH3:24])[CH3:22])[NH:25][CH2:26][C:27]2=[O:29])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58857938HCID 58857938, compound

Product 1

HCID 588579491-[(4-Fluorophenyl)methyl]-5-[2-(methoxymethylamino)ethyl]-2-piperazinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl N-{1-{[(tert-butoxycarbonyl)-(4-fluorobenzyl)amino]methyl}-3-[methoxy(methyl)amino]propyl}glycinate (1.63 g, 3.82 mmol) in CH2Cl2 (41 mL) was treated with TFA (12.6 mL) at 0° C. The mixture was stirred at ambient temperature under inert atmosphere for 2 h and then concentrated in vacuo. The resulting oil was suspended in water (46 mL) and treated, portion-wise, with solid K2CO3 (3.1 g). The reaction was heated to 100° C. for 30 min. After cooling to ambient temperature, the mixture was saturated with NaCl and extracted into CH2Cl2 three times. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to yield the title compound as an orange oil. 1H NMR (400 MHz, CDCl3) δ 7.29-7.23 (m, 2H), 7.05-6.99 (m, 2H), 4.63 (d, J=14.8 Hz, 1H), 4.47 (d, J=14.8 Hz, 1H), 3.62 (dt, J=17.2, 38.8 Hz, 2H), 3.47 (s, 3H), 3.12-3.10 (m, 1H), 3.08-2.94 (m, 2H), 2.71-2.62 (m, 2H), 2.55 (s, 3H), 1.82 (br s, 1H), 1.63 (dd, J=6.4, 12.4 Hz, 2H). ES MS (M+1)=296.4.

Workup

  1. concentrationconcentrated in vacuo
  2. additiontreated
  3. temperatureThe reaction was heated to 100° C. for 30 min
  4. temperatureAfter cooling to ambient temperature
  5. extractionextracted into CH2Cl2 three times
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e80ad06890e4c53973b43615a787b96
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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