Hydrochloric Acid → HCID 16044905, compound

HRID 1907387Notes

Reaction equation

HRID 1907387 reaction equation
Cl.CO.C(OC(=O)[NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([O:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][N:25]([C:28]3[C:36]4[CH:35]=[CH:34][S:33][C:32]=4[CH:31]=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)=[C:13]([O:37][CH3:38])[CH:12]=1)(C)(C)C.[OH-].[Na+]>ClCCl>[S:33]1[CH:34]=[CH:35][C:36]2[C:28]([N:25]3[CH2:24][CH2:23][N:22]([CH2:21][CH2:20][CH2:19][O:18][C:14]4[C:15]([CH3:17])=[CH:16][C:11]([NH2:10])=[CH:12][C:13]=4[O:37][CH3:38])[CH2:27][CH2:26]3)=[CH:29][CH:30]=[CH:31][C:32]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 16044904HCID 16044904, compound

Product 1

HCID 16044905HCID 16044905, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6N-hydrochloric acid (3 ml) was added to a methanol solution (10 ml) of {4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl}-carbamic acid tert-butyl ester (2.18 g, 4.3 mmol) and the mixture was stirred at room temperature overnight. After stirred at 60° C. for 15 minutes, the mixture was cooled to room temperature and a 6N aqueous sodium hydroxide solution was added thereto to neutralize it. Dichloromethane was added to the reaction mixture, and the substance extracted with dichloromethane was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:2→ethyl acetate). The purified product was concentrated to dryness under reduced pressure to obtain 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylaniline (1.26 g) as light yellow solid

Workup

  1. stirringAfter stirred at 60° C. for 15 minutes
  2. temperaturethe mixture was cooled to room temperature
  3. extractionthe substance extracted with dichloromethane
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:2→ethyl acetate)
  7. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-621687817f854e258cee7bf00c1e2496
Source dataset
uspto-grants-2013_12
Patent number
US08598162B2

Reaction notes

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