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Hydrochloric Acid → 4-[4-[4-(6-Methoxyhexyloxy)phenyl]piperazin-1-yl]benzoic acid dihydrochloride

HRID 1816720
Notes
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Reaction equation

HRID 1816720 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:32]=[CH:31][C:25]([C:26]([O:28]CC)=[O:27])=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1.[OH-].[Na+].O1CCCC1.[ClH:40]>C(O)C.O>[ClH:40].[ClH:40].[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:31][CH:32]=3)[CH2:18][CH2:17]2)=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 22494633HCID 22494633, compound

Product 1

HCID 696776354-[4-[4-(6-Methoxyhexyloxy)phenyl]piperazin-1-yl]benzoic acid dihydrochloride

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

A mixture of ethyl 4-[4-[4-(6-methoxyhexyloxy)phenyl]piperazin-1-yl]benzoate (3.00 g) in ethanol (30 ml) was treated with 1N-sodium hydroxide aqueous solution (6.81 ml) then the mixture was refluxed for 24 hours, during which period tetrahydrofuran (20 ml) and 1N-sodium hydroxide aqueous solution (6.81 ml) was added. After cooling, water was added to the mixture, and the acidity of the mixture was adjusted to pH 1 with 1N-hydrochloric acid. The resulting precipitate was filtered, washed with water and dried under reduced pressure to give 4-[4-[4-(6-methoxyhexyloxy)phenyl]piperazin-1-yl]benzoic acid dihydrochloride (2.25 g) as an ocher solid.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-de60567ccc1c4bcea091d66b966e2299
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06884868B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes