Hydrochloric Acid → HCID 59485092, compound

HRID 1850512Notes

Reaction equation

HRID 1850512 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([CH3:38])=[C:17]([CH3:37])[C:18]4[O:22][C:21]([CH2:24][N:25]5[CH2:34][CH2:33][C:28]6(OCC[O:29]6)[CH2:27][CH2:26]5)([CH3:23])[CH2:20][C:19]=4[C:35]=3[CH3:36])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl.C(OCC)(=O)C.Cl.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[C:16]([CH3:38])=[C:17]([CH3:37])[C:18]4[O:22][C:21]([CH2:24][N:25]5[CH2:34][CH2:33][C:28](=[O:29])[CH2:27][CH2:26]5)([CH3:23])[CH2:20][C:19]=4[C:35]=3[CH3:36])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21866389Hydrogen chloride-ethyl acetateHCID 59485080HCID 59485080, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 59485092HCID 59485092, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl acetate (2.0 mL) containing 8-({5-[4-(4-Methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methyl)-1,4-dioxa-8-azaspiro[4.5]decane (55 mg, 0.105 mmol) synthesized in Example 115, a solution of 4N hydrochloric acid-ethyl acetate (2.0 mL) was added, and the mixture was stirred at room temperature for 5 hours and at 50° C. for 2 hours. After that, 6N hydrochloric acid was (1.0 mL) was added thereto, and the mixture was further stirred at 70° C. for 2 hours. After cooled to room temperature, the reaction solution was poured into saturated sodium bicarbonate water, and extraction was performed using ethyl acetate. The extract was washed saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-72:28) and crystallized from ethyl acetate-hexane to give 25 mg of the title compound (yield 50%). Melting point was 123 to 127° C.

Workup

  1. additionwas added
  2. stirringthe mixture was further stirred at 70° C. for 2 hours
  3. temperatureAfter cooled to room temperature
  4. washThe extract was washed saturated saline
  5. customdried
  6. customThe solvent was removed under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-72:28)
  8. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-74a841e18f2642f0ab845d8e4c6d26ba
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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