2-(Dimethylamino)ethanol → HCID 69295047, compound

HRID 2403120Notes

Reaction equation

HRID 2403120 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[CH2:7]([O:18][CH2:19]Cl)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:21]([O-:29])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Na+]>CCCCCC>[C:21]([O-:29])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH:5][CH2:4][CH2:3][N+:2]([CH3:6])([CH3:1])[CH2:19][O:18][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 517055Sodium BenzoateHCID 12579126HCID 12579126, compound

Product 1

HCID 69295047HCID 69295047, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

2-(dimethylamino)ethanol (0.05 mol) was dissolved in anhydrous hexane (20 mL) and a solution of chloromethyl undecyl ether (0.05 mol) was added dropwise at room temperature. The reaction mixture was stirred for 15 minutes. The obtained precipitate was washed with dry hexane (40 mL). The material was used in the next step, without further purification. The prepared ammonium chloride was dissolved in water and an aqueous solution of sodium benzoate (0.07 mol) was added. The solution was stirring for 15 min. After 10 h, the reaction mixture was concentrated using a rotary evaporator. To a dry crude product, anhydrous acetone (30 mL) was added. The solid product was filtered and acetone was removed. The product was dried for 10 h at 50° C. in vacuum to obtain (2-hydroxyethyl)dimethylundecyloxymethylammonium benzoate as a grease in 80% yield. Thermogravimetric analysis: Tonset=127° C. 1H and 13C NMR (DMSO) were obtained.

Workup

  1. washThe obtained precipitate was washed with dry hexane (40 mL)
  2. customThe material was used in the next step, without further purification
  3. dissolutionThe prepared ammonium chloride was dissolved in water
  4. stirringThe solution was stirring for 15 min
  5. waitAfter 10 h
  6. concentrationthe reaction mixture was concentrated
  7. customa rotary evaporator
  8. dry with materialTo a dry crude product, anhydrous acetone (30 mL)
  9. additionwas added
  10. filtrationThe solid product was filtered
  11. customacetone was removed
  12. customThe product was dried for 10 h at 50° C. in vacuum

Sources & evidence

ORD record
ord-7ca18553795545fcb39e9ed6f667215f
Source dataset
uspto-grants-2014_08
Patent number
US08802596B2

Reaction notes

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