Acetic Anhydride → HCID 21837262, compound

HRID 1740618Notes

Reaction equation

HRID 1740618 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])[CH2:20][CH:19]3[C:31](=[O:33])[NH2:32])=[O:17])=[C:11]([O:34][C:35]([F:38])([F:37])[F:36])[CH:10]=2)[CH2:4][CH2:3]1.[C:39](OC(=O)C)(=[O:41])[CH3:40].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:39]([N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])[CH2:20][CH:19]3[C:31](=[O:33])[NH2:32])=[O:17])=[C:11]([O:34][C:35]([F:36])([F:37])[F:38])[CH:10]=2)[CH2:4][CH2:3]1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 21837258HCID 21837258, compound

Product 1

HCID 21837262HCID 21837262, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(4-piperidinyloxy)-2-(trifluoromethoxy)phenylacetyl)-2-carbamoyl-4-(2-methylphenyl)piperazine hydrochloride (0.30 g, 0.5 mmol) from Example 33 in CH2Cl2 (50 mL) was added acetic anhydride (0.10 mL, 1.0 mmol) and DIEA (0.17 mL, 1.0 mmol). The solution was stirred at ambient temperature for 1 h and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed with 0.25 M aqueous citric acid (50 mL), H2O (25 mL), and saturated aqueous NaHCO3 (75 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give the title compound as an amorphous solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (100 mL)
  3. washwashed with 0.25 M aqueous citric acid (50 mL), H2O (25 mL), and saturated aqueous NaHCO3 (75 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7ee2d06a9c6f491d84724a16cc003af8
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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