Hydrochloric Acid → 4-{5-[1-(4-Methyl-piperazin-1-ylmethyl)-cyclopropyl]-4-phenyl-isoxazol-3-yl}-phenol

HRID 2378052Notes

Reaction equation

HRID 2378052 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3([CH2:25][N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH2:24][CH2:23]3)[O:13][N:12]=2)=[CH:7][CH:6]=1.Cl.[OH-].[Na+]>C(O)(C)C>[CH3:32][N:29]1[CH2:28][CH2:27][N:26]([CH2:25][C:22]2([C:14]3[O:13][N:12]=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=4)[C:15]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23][CH2:24]2)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 689564541-{1-[3-(4-Methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropylmethyl}-4-methyl-piperazine

Product 1

HCID 1363896464-{5-[1-(4-Methyl-piperazin-1-ylmethyl)-cyclopropyl]-4-phenyl-isoxazol-3-yl}-phenol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture consisting of 1-{1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropylmethyl}-4-methyl-piperazine (this example, Step B) in isopropanol is added 6 N hydrochloric acid solution. The mixture is stirred at room temperature overnight. The mixture is titrated to pH 8 with an aqueous sodium hydroxide solution and is extracted with ethyl acetate. The organic layer is separated and dried over anhydrous sodium sulfate. The mixture is filtered and the filtrate is concentrated under reduced pressure. The concentrate is purified to afford the title compound 1H NMR (400 MHz, CDCl3) δ 7.40-7.20 (m, 7H), 6.70 (d, 2H), 2.45 (m, 8H), 2.25 (s, 3H), 1.05 (m, 2H), 0.78 (m, 2H); MS (EH+) m/z 390 (MH+.)

Workup

  1. extractionis extracted with ethyl acetate
  2. customThe organic layer is separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe mixture is filtered
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe concentrate is purified

Sources & evidence

ORD record
ord-0a4448c9c1834f059b66be5e6d967d78
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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