Hydrochloric Acid → 3'-(Benzyloxy)-2-isopropylamino-acetophenone hydrochloride

HRID 1995411Notes

Reaction equation

HRID 1995411 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12](=[O:15])[CH2:13]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]([NH2:22])([CH3:21])[CH3:20].[ClH:23].O>C(O)C>[ClH:23].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:12](=[O:15])[CH2:13][NH:22][CH:19]([CH3:21])[CH3:20])[CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6363IsopropylamineHCID 880311-(3-(Benzyloxy)phenyl)-2-bromoethanone

Product 1

HCID 201344613'-(Benzyloxy)-2-isopropylamino-acetophenone hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 425 ml of ethanol, 64 g of 3-benzyloxyphenacyl bromide and 212 ml of iso-propylamine are stirred at 5° C. under N2 atmosphere, and the temperature is allowed to rise to 12° C. After 0.75 minutes, the clear solution is poured into 2 liters of crushed ice containing 500 ml of concentrated HCl and 1.5 liters of H2O. The mixture is stirred for 20 minutes, filtered and the solid is washed with water to afford 3'-(benzyloxy)-2-isopropylamino-acetophenone hydrochloride, mp 213°-215° C. dec. A 5 g.-sample of this material is stirred in 50 ml of methanol, and the mixture is cooled in ice and neutralized with 10% NaOH until a clear solution is obtained. To this solution, 2 g of NaBH4 is added and after 0.75 hours of stirring, the mixture is evaporated in vacuo, and the resulting solid is collected and washed with H2O. This gives, after drying, 4.4 g of m-(benzyloxy)-β-[(isopropylamino)methyl]benzyl alcohol, mp 83°-85° C.

Workup

  1. customto rise to 12° C
  2. filtrationfiltered
  3. washthe solid is washed with water

Sources & evidence

ORD record
ord-e7ea9cd458f043f79c84b51971b62b75
Source dataset
uspto-grants-1983_09
Patent number
US04404222

Reaction notes

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