Acetic Acid → HCID 19894546, compound

HRID 893021Notes

Reaction equation

HRID 893021 reaction equation
C([O:4][C:5]1[C:6]([CH3:36])=[C:7]([CH3:35])[C:8]2[O:13][C:12]([CH2:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[C:29]([NH:30][CH2:31][CH3:32])=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:20][CH2:19]3)=[O:17])([CH3:14])[CH2:11][CH2:10][C:9]=2[C:33]=1[CH3:34])(=O)C.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CO>[OH:4][C:5]1[C:6]([CH3:36])=[C:7]([CH3:35])[C:8]2[O:13][C:12]([CH2:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[C:29]([NH:30][CH2:31][CH3:32])=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:20][CH2:19]3)=[O:17])([CH3:14])[CH2:11][CH2:10][C:9]=2[C:33]=1[CH3:34]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 19894535HCID 19894535, compound

Product 1

HCID 19894546HCID 19894546, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[[6-(acetyloxy)-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl]acetyl]-4-[3-(ethylamino)-2-pyridinyl]-piperazine (EXAMPLE 68, 0.80 g) in methanol (20 ml) is mixed with potassium carbonate (10% aqueous, 1.5 ml) and stirred for 3.5 hr at 20°-25° under a nitrogen atmosphere. Then acetic acid (0.2 ml) is added and the solution is concentrated. The residue is partitioned between methylene chloride and potassium bicarbonate (1N). The organic extracts are combined and washed with water, dried over magnesium sulfate and concentrated to give the title compound.

Workup

  1. concentrationthe solution is concentrated
  2. customThe residue is partitioned between methylene chloride and potassium bicarbonate (1N)
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a4ccfe3f67ba49d481052db7b7c9f329
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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