Isopropanol → 2-(Benzyloxy)ethanamine hydrochloride

HRID 1386636Notes

Reaction equation

HRID 1386636 reaction equation
Cl.[CH2:2]([CH2:4][NH2:5])[OH:3].[Na].[CH2:7]([Cl:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O)(C)C>C1(C)C=CC=CC=1>[ClH:14].[C:8]1([CH2:7][O:3][CH2:2][CH2:4][NH2:5])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7503Benzyl ChlorideHCID 74819Ethanolamine HydrochlorideHCID 5360545Sodium2×

Product 1

HCID 27947862-(Benzyloxy)ethanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethanolamine hydrochloride (20 g, 0.21 mol) in toluene (100 mL) was treated with sodium metal (pellets washed with hexane) (10.14 g, 0.44 mL). The reaction was refluxed until the sodium metal was no longer present. The mixture was cooled and benzyl chloride (24.17 mL, 0.21 mmol) was added, the reaction was stirred at room temperature overnight. The reaction mixture was filtered and the solid washed with toluene. The filtrate was cooled to 0° C. and HCl gas was bubbled in for 10 minutes. A white precipitate was obtained and filtered. The solid was recrystallized using 70 mL of isopropyl alcohol (10.4 g, 0.056 mol); MS-CI 188 (m+1).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe reaction mixture was filtered
  3. washthe solid washed with toluene
  4. temperatureThe filtrate was cooled to 0° C.
  5. customHCl gas was bubbled in for 10 minutes
  6. customA white precipitate was obtained
  7. filtrationfiltered
  8. customThe solid was recrystallized

Sources & evidence

ORD record
ord-be8077d18bea4174aea37a593f840722
Source dataset
uspto-grants-2001_07
Patent number
US06265382B1

Reaction notes

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