Hydrochloric Acid → HCID 22494632, compound

HRID 1816707Notes

Reaction equation

HRID 1816707 reaction equation
C([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][CH:26]([S:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[CH2:30]([S:29][CH:26]1[CH2:25][CH2:24][N:23]([C:20]2[CH:19]=[CH:18][C:17]([N:14]3[CH2:13][CH2:12][N:11]([C:8]4[CH:7]=[CH:6][C:5]([C:4]([OH:33])=[O:3])=[CH:10][CH:9]=4)[CH2:16][CH2:15]3)=[CH:22][CH:21]=2)[CH2:28][CH2:27]1)[CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69677646HCID 69677646, compound

Product 1

HCID 22494632HCID 22494632, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[1-[4-(4-propylthiopiperidin-1-yl)phenyl]piperazin-4-yl]benzoic acid ethyl ester (1.22 g) in a mixture of ethanol (10 ml) and tetrahydrofuran (40 ml) was added 10% aqueous NaOH (2.1 ml) and 1N-NaOR (10 ml), and the mixture was refluxed for 6 hours. The reaction mixture was cooled and adjusted to pH 2.5-3.0 with 1N-HCl. The resulting precipitates were collected by filtration, washed in turn with water (30 ml) and IPE (50 ml) and dried in vacuo to give 4-[1-[4-(4-propylthiopiperidin-1-yl)phenyl]piperazin-4-yl]benzoic acid (0.99 g).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed in turn with water (30 ml) and IPE (50 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-bf625efab19648a59cfe86b282caa244
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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