Hydrochloric Acid → (R)-N-(2-(2-(10H-Phenothiazin-10-yl)ethoxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

HRID 2226741Notes

Reaction equation

HRID 2226741 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][N:17]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:24][C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].[Cl:33]CCl.Cl>C(O)C>[ClH:33].[CH:19]1[C:18]2[N:17]([CH2:16][CH2:15][O:14][CH2:13][CH2:12][N:8]3[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[S:24][C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 11048193(R)-N-(2-(2-(10H-phenothiazin-10-yl)ethoxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

Product 1

HCID 24842634(R)-N-(2-(2-(10H-Phenothiazin-10-yl)ethoxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (0.8 g, 1.8 mmol) was dissolved in ethanol (15 ml) and a 4 N sodium hydroxide solution (2 ml) was added. The mixture was stirred vigorously at room temperature for 4 h. The solvent was evaporated in vacuo to give an oily residue. Dichloromethane (100 ml) was added and the mixture was cooled on an ice-bath. A concentrated hydrochloric acid solution (1 ml) was added. The mixture was stirred vigorously for a few minutes and the phases were separated. The organic phase was dried over sodium sulphate and the solvent was evaporated in vacuo. The residue was re-evaporated with dichloromethane, dissolved in dichloromethane and left overnight at 4° C. The solid formed was isolated by filtration to give 0.6 g of the title compound as a solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give an oily residue
  3. temperaturethe mixture was cooled on an ice-bath
  4. stirringThe mixture was stirred vigorously for a few minutes
  5. customthe phases were separated
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was re-evaporated with dichloromethane
  9. dissolutiondissolved in dichloromethane
  10. waitleft overnight at 4° C
  11. customThe solid formed
  12. customwas isolated by filtration

Sources & evidence

ORD record
ord-040454ce7759426abd05bd85edca6037
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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