Sodium Hydroxide → HCID 22675550, compound

HRID 1006028Notes

Reaction equation

HRID 1006028 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:27][CH:28]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22675500HCID 22675500, compound

Product 1

HCID 22675550HCID 22675550, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-[3-(2-(benzylamino)phenyl)propyl]benzoate (1 g) in methanol (50 ml) was added 1N sodium hydroxide (13.4 ml). The mixture was stirred for 2 hours, heated at reflux for 10 minutes, the solvent was evaporated, the residue mixed with water (50 ml) and acidified to pH 4 with 2N HCl. The mixture was extracted with ethyl acetate (3×20 ml) and the extracts washed with brine (2×20 ml), dried (MgSO4), filtered and evaporated. The residue was triturated with petroleum ether (60-80) (25 ml) to give the title compound (0.55 g; 118° C.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 10 minutes
  3. customthe solvent was evaporated
  4. additionthe residue mixed with water (50 ml)
  5. extractionThe mixture was extracted with ethyl acetate (3×20 ml)
  6. washthe extracts washed with brine (2×20 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was triturated with petroleum ether (60-80) (25 ml)

Sources & evidence

ORD record
ord-af789b8b74f3447eab1dc80aafe3d985
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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