Hydrochloric Acid → HCID 18669078, compound

HRID 1058970Notes

Reaction equation

HRID 1058970 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[C:7]2[CH2:20][CH2:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]([O:33]CC)=[O:32])[CH2:26][CH2:25]1)=[O:23].O.Cl>CO>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[C:7]2[CH2:20][CH2:21][C:22]([N:24]1[CH2:25][CH2:26][N:27]([CH2:30][C:31]([OH:33])=[O:32])[CH2:28][CH2:29]1)=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 53962259HCID 53962259, compound

Product 1

HCID 18669078HCID 18669078, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (320 mg) was added to a solution of ethyl 4-{3-[5-chloro-2-(4-chlorophenyl)-1H-indol-3-yl]-1-oxopropyl}piperazine-1-acetate (Example 109, 350 mg, 0.72 mmol) in methanol and the mixture was stirred at room temperature overnight. Water was added and the pH was adjusted to 7.0 with hydrochloric acid (2M). The mixture was extracted with ethyl acetate, the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was crystallised from ethyl acetate:methanol (99:1) to give the title compound as a pale solid (300 mg, 90%). 1H NMR (250 MHz, CD3OD) δ2.20-2.26 (2H, m), 2.92-2.97 (2H, m), 3.10-3.25 (4H, m), 3.55-3.60 (2H, m), 3.90-4.01 (4H, m), 7.10 (1H, dd, J 8.8, 2.0 Hz), 7.38 (1H, d, J 8.8 Hz), and 7.45-7.60 (5H, m). m/z (ES+) 460, 462 (M+1).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe combined organic fractions were dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was crystallised from ethyl acetate:methanol (99:1)

Sources & evidence

ORD record
ord-0cac359f43f34ce29d58ba1604833ddc
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

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