Hydrochloric Acid → HCID 66885401, compound

HRID 1801671Notes

Reaction equation

HRID 1801671 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-239ec07dcaa249f19e7d9b9b9eb255ac
Source dataset
uspto-grants-2013_01
Patent number
US08349840B2

Reaction notes

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