Hydrochloric Acid → HCID 70163771, compound

HRID 1017686Notes

Reaction equation

HRID 1017686 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)[CH2:15][CH2:14]2)[CH3:12])=[CH:7][C:6]=1[O:29][CH3:30])(=[O:3])C.Cl>[OH-].[Na+].C(O)C.C(OCC)(=O)C>[OH2:3].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)[CH2:15][CH2:14]2)[CH3:12])=[CH:7][C:6]=1[O:29][CH3:30].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)[CH2:15][CH2:14]2)[CH3:12])=[CH:7][C:6]=1[O:29][CH3:30]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 53967234HCID 53967234, compound

Product 1

HCID 70163771HCID 70163771, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-[1-(4-acetoxy-3-methoxyphenyl)ethyl]-4-(2-quinolinyl)piperazine(4.7 g) in 50% sodium hydroxide solution (8 ml) and 50% aqueous ethanol (50 ml) was heated at 50° C. for 24 hrs, under nitrogen. The reaction mixture was diluted with ethyl acetate (150 ml), neutralized with 10% hydrochloric acid and dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was flash chromatographed (silica gel), eluting with 1% acetone/1% methanol/dichloromethane. The appropriate fractions were collected and concentrated to afford 1.8 g (43%) of product, mp 53-54° C.

Workup

  1. dry with materialdried over anhydrous sodium sulfate
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customchromatographed (silica gel)
  5. washeluting with 1% acetone/1% methanol/dichloromethane
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9f09e4b2df5f4cf69f2987c8aa2bc633
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

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