Hydrochloric Acid → HCID 14391179, compound

HRID 1381525Notes

Reaction equation

HRID 1381525 reaction equation
[BH4-].[Na+].[CH3:3][N:4]([CH3:24])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:20][CH2:21][CH2:22][OH:23])[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:7][CH:6]=1.Cl.[OH-].[Na+]>C(O)C.CO>[CH3:3][N:4]([CH3:24])[C:5]1[CH:6]=[CH:7][C:8]([CH:11]([NH:20][CH2:21][CH2:22][OH:23])[CH:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[OH:13])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 14391178HCID 14391178, compound

Product 1

HCID 14391179HCID 14391179, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Sodium borohydride (0.22 g, 0.0057 mole) was added in several portions to a stirred suspension of 2-(4-dimethylaminophenyl)-2-(hydroxyethylamino)acetophenone (0.85 g, 0.00285 mole) in 50 ml of absolute ethanol and the mixture stirred at ambient temperature for 0.5 hr. The mixture was then heated to reflux temperature for 0.5 hr, cooled to ambient temperature, and 6N HCl solution added until the mixture was neutral. The mixture was concentrated to give a yellow solid. This solid was dissolved in a minimum volume of methanol and acidified with 6N hydrochloric acid to give a clear yellow solution. This solution was brought to pH 8 with 6N sodium hydroxide solution, cooled by the addition of ice, and the white solid collected to obtain 0.54 g (63%) of the desired product. Recrystallization from acetoneisopropyl ether gave 0.25 g of title compound, m.p. 147°-148° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux temperature for 0.5 hr
  3. temperaturecooled to ambient temperature
  4. concentrationThe mixture was concentrated
  5. customto give a yellow solid
  6. customto give a clear yellow solution
  7. temperaturecooled by the addition of ice
  8. customthe white solid collected

Sources & evidence

ORD record
ord-a56cb6bc44814fdfa8d110db87ad62b5
Source dataset
uspto-grants-1989_02
Patent number
US04803200

Reaction notes

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