Hydrochloric Acid → HCID 14129809, compound

HRID 1252080Notes

Reaction equation

HRID 1252080 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:23](=[O:30])[CH2:24][CH2:25][O:26]C(=O)C)[S:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:2]1.[OH-].[Na+].Cl>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:23](=[O:30])[CH2:24][CH2:25][OH:26])[S:20][CH:21]=3)[CH2:14][CH2:15]2)=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14129793HCID 14129793, compound

Product 1

HCID 14129809HCID 14129809, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-[4-(3-indolyl)piperidinomethyl]-2-(3acetoxypropionylamino)thiazole (1.1 g) were added ethanol (20 ml) and 1N aqueous solution of sodium hydroxide (2.6 ml) and the mixture was stirred at an ambient temperature for 3.5 hours. 1N hydrochloric acid (2.6 ml) was added thereto and ethanol was evaporated. The residue was extracted with a mixture of chloroform and methanol (10:1 V/V) and the extract was dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (10:1 V/V) to give 4-[4-(3-indolyl)piperidinomethyl]-2(3-hydroxypropionylamino)thiazole (290 mg).

Workup

  1. customethanol was evaporated
  2. extractionThe residue was extracted with a mixture of chloroform and methanol (10:1 V/V)
  3. dry with materialthe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (10:1 V/V)

Sources & evidence

ORD record
ord-63e47883ac1b4bffbb68c83e61cf395f
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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