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Hydrochloric Acid → 4-[4-(3,3-Diphenylprop-2-en-1-yl)piperazin-1-yl]benzoic acid

HRID 1968600
Notes
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Reaction equation

HRID 1968600 reaction equation
[C:1]1([C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+].Cl>O1CCCC1.CO.O>[C:27]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=3)[CH2:14][CH2:15]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67144443Ethyl 4-(4-(3,3-diphenylallyl)piperazin-1-yl)benzoate

Product 1

HCID 671447144-[4-(3,3-Diphenylprop-2-en-1-yl)piperazin-1-yl]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 21899815
MeOH tetrahydrofuran
Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of EXAMPLE 1C (10.00 g, 23.4 mmol) in tetrahydrofuran/methanol (100/50 mL) was added solution of lithium hydroxide monohydrate (2.59 g, 70 mmol) in water (30 mL). The reaction mixture was stirred at 60° C. for 16 hours, then was cooled to room temperature and the organic solvents were concentrated. The white solid residue was dissolved in hot water and then the product was neutralized with HCl (3 equivalents). After cooling to room temperature, the precipitate was filtered off, washed with water and dried in a vacuum oven overnight at 40° C.

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationthe organic solvents were concentrated
  3. dissolutionThe white solid residue was dissolved in hot water
  4. temperatureAfter cooling to room temperature
  5. filtrationthe precipitate was filtered off
  6. washwashed with water
  7. customdried in a vacuum oven overnight at 40° C.

Sources & evidence

ORD record
ord-f868e359823745e8bcd70127cd13138c
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08426422B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes