Hydrochloric Acid → (R)-1-(2-(((2-Phenyl-1,2,3,4-tetrahydro-1-naphthylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

HRID 1683742Notes

Reaction equation

HRID 1683742 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][N:15]=[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18][CH:17]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:35]CCl>C(O)C>[ClH:35].[C:26]1([CH:17]2[CH2:18][CH2:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:16]2=[N:15][O:14][CH2:13][CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54388268HCID 54388268, compound

Product 1

HCID 88379959(R)-1-(2-(((2-Phenyl-1,2,3,4-tetrahydro-1-naphthylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (0.6 g, 1.5 mmol) was dissolved in ethanol (10 ml) and 4N sodium hydroxide (1.1 ml) was added. The mixture was stirred at ambient temperature for 4 h and excess concentrated hydrochloric acid was added followed by dichloromethane (300 ml). The mixture was dried (MgSO4) and the solvent evaporated in vacuo to give a residue which was re-evaporated with acetone and recrystallised from acetone. This afforded 0.5 g of the title compound as a solid.

Workup

  1. dry with materialThe mixture was dried (MgSO4)
  2. customthe solvent evaporated in vacuo
  3. customto give a residue which
  4. customwas re-evaporated with acetone
  5. customrecrystallised from acetone

Sources & evidence

ORD record
ord-7ce5ad018a6745e7b4dcb50749b8e16f
Source dataset
uspto-grants-1997_06
Patent number
US05639766

Reaction notes

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