Ethanolamine → 2-(3-Benzyloxy-propylamino)-ethanol

HRID 559347Notes

Reaction equation

HRID 559347 reaction equation
[I-].[Na+].Br[CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:15]([CH2:17][NH2:18])[OH:16]>C(O)C>[CH2:8]([O:7][CH2:6][CH2:5][CH2:4][NH:18][CH2:17][CH2:15][OH:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 5238Sodium IodideHCID 2776064Benzyl 3-Bromopropyl Ether

Product 1

HCID 669993512-(3-Benzyloxy-propylamino)-ethanolYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium iodide (1.67 g, 11.1 mmol) was added to a solution of benzyl 3-bromopropyl ether (26.0 g, 111 mmol) and ethanolamine (35.0 g, 556 mmol) in ethanol (250 ml). The reaction mixture was heated at reflux for 1 h, then cooled to room temperature and evaporated under vacuum. The residue was partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The aqueous layer was basified with 40% aq. sodium hydroxide solution and extracted three times with ethyl acetate. The organic phases were pooled, dried (MgSO4), filtered, and evaporated to afford the title compound (20.9 g, 90%). Light yellow liquid, MS (ISP)=210.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. customevaporated under vacuum
  4. customThe residue was partitioned between sat. aq. ammonium chloride solution and ethyl acetate
  5. extractionextracted three times with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-395451ae0cc948f2b3539dea46296605
Source dataset
uspto-grants-2011_11
Patent number
US08063042B2

Reaction notes

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