Trifluoroacetic acid → HCID 22288423, compound

HRID 968246Notes

Reaction equation

HRID 968246 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:12]=[C:13]([NH:18]C(=O)OC(C)(C)C)[CH:14]=[C:15]([CH3:17])[CH:16]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:12]=[C:13]([CH:14]=[C:15]([CH3:17])[CH:16]=2)[NH2:18])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22288425Tert-butyl 3-[(4-acetylpiperazin-1-yl)methyl]-5-methylphenylcarbamate

Product 1

HCID 22288423HCID 22288423, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-[(4-acetylpiperazin-1-yl)methyl]-5-methylphenylcarbamate (306 mg, 0.88 mmol) in CH2Cl2 (4 mL) was added TFA (4 mL) at room temperature. After 2 hours the mixture was concentrated. The residue was taken up in saturated NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated to give 3-[(4-acetylpiperazin-1-yl)methyl]-5-methylaniline as a white solid. 1H-NMR (300 MHz, CDCl3) δ 6.52 (s, 1H), 6.48 (s, 1H), 6.43 (s, 1H), 3.62 (m, 4H), 3.45 (m, 2H), 3.39 (s, 2H), 2.40 (m, 4H), 2.25 (s, 3H), 2.08 (s, 3H).

Workup

  1. concentrationAfter 2 hours the mixture was concentrated
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20bf7ca4cfab45a5ab8a254c9f417a02
Source dataset
uspto-grants-2005_10
Patent number
US06958340B2

Reaction notes

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