Hydrochloric Acid → HCID 66885401, compound

HRID 1916243Notes

Reaction equation

HRID 1916243 reaction equation
[OH-].[Li+].CO.[S:5]1[CH:9]=[CH:8][C:7]2[C:10]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][O:23][C:24]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=[C:26]([C:34]([O:36]CC)=[O:35])[CH:25]=4)[CH2:16][CH2:15]3)=[CH:11][CH:12]=[CH:13][C:6]1=2.[ClH:39]>O>[ClH:39].[S:5]1[CH:9]=[CH:8][C:7]2[C:10]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][O:23][C:24]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=[C:26]([C:34]([OH:36])=[O:35])[CH:25]=4)[CH2:16][CH2:15]3)=[CH:11][CH:12]=[CH:13][C:6]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium Hydroxide2×HCID 66885632HCID 66885632, compound

Product 1

HCID 66885401HCID 66885401, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An aqueous solution of 4N lithium hydroxide (3 ml) was added to a methanol solution (7 ml) of ethyl 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-quinolin-2-carboxylate (1.5 g), followed by stirring at room temperature overnight. Then, water (10 ml) and aqueous solution (3 ml) of 4N lithium hydroxide were further added, followed by stirring at 50° C. for 11 hours. The reaction mixture was cooled in an ice-bath, and an aqueous solution (4 ml) of 6N-HCl was added thereto. Then, crystals precipitated were filtered out, washed with water and dried to obtain 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]quinolin-2-carboxylic acid hydrochloride (1.43 g, yield: 98%) as white powder.

Workup

  1. stirringby stirring at 50° C. for 11 hours
  2. temperatureThe reaction mixture was cooled in an ice-bath
  3. customThen, crystals precipitated
  4. filtrationwere filtered out
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-38d428f19c054f47809c879b63fee6bf
Source dataset
uspto-grants-2013_12
Patent number
US08618109B2

Reaction notes

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