Hydrochloric Acid → 3-Amino-1-Phenoxy-2-Propanol Hydrochloride

HRID 544419Notes

Reaction equation

HRID 544419 reaction equation
C1(=O)[N:5]([CH2:6][CH:7]([OH:16])[CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)C(=O)CC1.C(O)C.[ClH:22]>>[ClH:22].[NH2:5][CH2:6][CH:7]([OH:16])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2927851-(2-Hydroxy-3-(phenoxy)propyl)succinimide

Product 1

HCID 27250723-Amino-1-Phenoxy-2-Propanol HydrochlorideYield 69%

Procedure

1-Succinimido-3-phenoxy-2-propanol (16 gm, 0.06 mole) was dissolved in 100 mL conc. HCl and 100 mL ethanol and heated to reflux for 6 hours. After the reaction, the mixture was evaporated to a white residue which was thentaken up in 25 mL water and washed with 3×50 mL ether. The aqueous phase was then evaporated and the white-residue recrystallized from ethanol to provide 8.3 gm (69%) of white crystals: mp 226°-228°. The NMR spectrum was consistent with the assignedstructure and the elemental analysis was consistent with the molecular formula C9H14NO2Cl.

Workup

  1. temperatureto reflux for 6 hours
  2. customAfter the reaction
  3. customthe mixture was evaporated to a white residue which
  4. washwashed with 3×50 mL ether
  5. customThe aqueous phase was then evaporated
  6. customthe white-residue recrystallized from ethanol

Sources & evidence

ORD record
ord-c5c6f8834cd240d7a88e4578192bfe8f
Source dataset
uspto-grants-1984_05
Patent number
US04450173

Reaction notes

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