Hydrochloric Acid → HCID 18918325, compound

HRID 864815Notes

Reaction equation

HRID 864815 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][O:10][C:11]1[CH:25]=[CH:24][C:14]([O:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:13][CH:12]=1.[OH-].[Na+].CO.Cl>O>[CH3:26][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][O:10][C:11]1[CH:25]=[CH:24][C:14]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 18918572HCID 18918572, compound

Product 1

HCID 18918325HCID 18918325, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing ethyl 4-[4-[(4-dimethylaminopyrid-3-yl)methoxy]phenoxy]butanoate (25 mg), aqueous sodium hydroxide (1M, 0.2 ml), methanol (0.5 ml) and water (0.5 ml) was stirred for 3 hours then neutralised with hydrochloric acid (1M, 0.2 ml) and concentrated. The residue was dissolved in dichloromethane (5 ml), filtered, and the filtrate was concentrated to give the title compound (17 mg) as a colourless gum. NMR (d6DMSO+d4AcOH): δ2.0(2H,q); 2.4(2H,t); 3.35(6H,s); 3.95(2H,t); 5.1(2H,s); 6.8-7.0(4H, dd +1H,m); 8.15(1H,dd); 8.3(1H,d); m/e 331(M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane (5 ml)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-aa2147d6c8814af5974b785f29965e84
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

Loading…