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

HRID 516810Notes

Reaction equation

HRID 516810 reaction equation
[OH:1][CH:2]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][N:4]1C(=O)CCC1=O.[ClH:19]>C(O)C.O>[ClH:19].[NH2:4][CH2:3][CH:2]([OH:1])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

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

Product 1

HCID 27250723-Amino-1-Phenoxy-2-Propanol Hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-(2-hydroxy-3-phenoxypropyl)pyrrolidine-2,5-dione (3.5 g, 13.1 mmol) (as shown at 3 above) in HCl (12N, 20 mL) and ethanol (20 mL) was heated to reflux for 6 hours. After thin layer chromatography (TLC) showed the reaction was complete, the mixture was concentrated in vacuum to give a white residue, which was taken up in water (20 mL) and washed with ether (3*50 mL). The aqueous phase was concentrated to give crude product, which was crystallized from methanol to give 2.9 g of 1-amino-3-phenoxypropan-2-ol hydrochloride (as shown at 4).

Workup

  1. temperatureto reflux for 6 hours
  2. concentrationthe mixture was concentrated in vacuum
  3. customto give a white residue, which
  4. washwashed with ether (3*50 mL)
  5. concentrationThe aqueous phase was concentrated
  6. customto give crude product, which
  7. customwas crystallized from methanol

Sources & evidence

ORD record
ord-94e1cbc435334c1ba7ded2023129ca7e
Source dataset
uspto-grants-2015_08
Patent number
US09115082B2

Reaction notes

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