Hydrochloric Acid → HCID 66759942, compound

HRID 1850405Notes

Reaction equation

HRID 1850405 reaction equation
Cl.C1COCC1.[Si]([O:14][C:15]1[C:19]2[C:20]([CH3:40])=[C:21]([N:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[CH2:28][CH2:27]3)[C:22]([CH3:25])=[C:23]([CH3:24])[C:18]=2[O:17][CH:16]=1)(C(C)(C)C)(C)C>O.C(=O)(O)[O-].[Na+]>[CH3:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([N:29]2[CH2:28][CH2:27][N:26]([C:21]3[C:22]([CH3:25])=[C:23]([CH3:24])[C:18]4[O:17][CH2:16][C:15](=[O:14])[C:19]=4[C:20]=3[CH3:40])[CH2:31][CH2:30]2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 66759806HCID 66759806, compound

Product 1

HCID 66759942HCID 66759942, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 86585896Sodium bicarbonate waterSolvent

Procedure

1N hydrochloric acid (5 mL) was added to a solution of THF (25 mL) containing 1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4,6,7-trimethyl-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine (560 mg, 1.16 mmol) synthesized in Reference Example 108, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was diluted with saturated sodium bicarbonate water. THF in the reaction mixture was removed under reduced pressure, and the residue was extracted using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5 to 85/15) to give 310 mg of the title compound (yield: 73%).

Workup

  1. customsynthesized in Reference Example 108
  2. customTHF in the reaction mixture was removed under reduced pressure
  3. extractionthe residue was extracted
  4. washThe extract was washed with saturated saline
  5. customdried
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5 to 85/15)

Sources & evidence

ORD record
ord-c756d3e6f4744070ae645e47740e963b
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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