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

HRID 655524Notes

Reaction equation

HRID 655524 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-10209628304248009594654e1c0e76ee
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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