Hydrochloric Acid → (R)-1-(2-(((2-Phenylcyclohex-2-enylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

HRID 1683736Notes

Reaction equation

HRID 1683736 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[CH2:21][CH2:20][CH2:19][CH:18]=[C:17]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:31]CCl>C(O)C>[ClH:31].[C:22]1([C:17]2[C:16](=[N: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)[CH2:21][CH2:20][CH2:19][CH:18]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54444134(R)-1-(2-(((2-phenylcyclohex-2-enylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester

Product 1

HCID 88380200(R)-1-(2-(((2-Phenylcyclohex-2-enylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (0.4 g, 1.1 mmol) was dissolved in ethanol (10 ml) and 4N sodium hydroxide (1 ml) was added. The mixture was stirred at ambient temperature for 3 h and excess concentrated hydrochloric acid was added followed by dichloromethane (400 ml). The suspension was dried (MgSO4) and the solvent evaporated in vacuo. The residue was re-evaporated with acetone, dissolved in acetone (10 ml) and left for crystallisation. This afforded 0.17 g of the title compound as a solid.

Workup

  1. dry with materialThe suspension was dried (MgSO4)
  2. customthe solvent evaporated in vacuo
  3. customThe residue was re-evaporated with acetone
  4. dissolutiondissolved in acetone (10 ml)
  5. waitleft for crystallisation

Sources & evidence

ORD record
ord-e31aaec937b64afb9e685bb886e75136
Source dataset
uspto-grants-1997_06
Patent number
US05639766

Reaction notes

Loading…