N-Methyldiethanolamine → HCID 15521496, 화합물

HRID 1604215노트

반응식

HRID 1604215 반응식
[OH-].[Na+].[CH3:3][N:4]([CH2:8][CH2:9][OH:10])[CH2:5][CH2:6][OH:7].CS(O[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=O)=O>O1CCCC1>[CH2:16]([O:7][CH2:6][CH2:5][N:4]([CH2:8][CH2:9][O:10][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])[CH3:3])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

참가 물질

5

반응물 3

HCID 7767N-MethyldiethanolamineHCID 14798Sodium HydroxideHCID 1386911-Tetradecanol, methanesulfonate

생성물 1

HCID 15521496HCID 15521496, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A dry vessel under an argon atmosphere was charged with 1.15 g (29 mmol, 2.2 eq) 60% sodium hydroxide in mineral oil. A positive argon pressure was maintained throughout the experiment. The mineral oil was removed by trituration with 3×12 mL dry hexane, then 80 mL anhydrous tetrahydrofuran were added and stirring was initiated. A solution of N-methyldiethanolamine (1.55 g, 13 mmol) in 15 mL anhydrous tetrahydrofuran was added dropwise to the magnetically stirred suspension at room temperature, followed by reflux overnight. A solution of tetradecyl methane sulfonate (9.37 g, 32 mmol, 2.5 eq) in 23 mL anhydrous tetrahydrofuran was added and the reaction was maintained at reflux for three days. The reaction mixture was then cooled, and the slurry vacuum filtered through a 0.75 cm pad of Celite. The reaction vessel and filtration apparatus were rinsed with 100 mL tetrahydrofuran. The combined filtrates were evaporated to yield the crude product which was purified using silica gel (4.5×35 cm bed) in conjunction with a step gradient of ethyl ether:hexane (10:90 to 100:0). Pure fractions were determined by aliquot thin layer chromatography (2:1 ether:hexane). These fractions were pooled, evaporated and resuspended in neat ether and dried with a small amount of magnesium sulfate. Filtration through a 0.2 μm PTFE filter, then rotary evaporation followed by high vacuum treatment yielded pure [bis-(2-tetradecyloxyethyl)-methyl amine] (DEMOA) (2.30 g, 35%).

후처리

  1. temperatureA positive argon pressure was maintained throughout the experiment
  2. customThe mineral oil was removed by trituration with 3×12 mL dry hexane
  3. addition80 mL anhydrous tetrahydrofuran were added
  4. temperatureby reflux overnight
  5. temperaturethe reaction was maintained
  6. temperatureat reflux for three days
  7. temperatureThe reaction mixture was then cooled
  8. filtrationthe slurry vacuum filtered through a 0.75 cm pad of Celite
  9. filtrationThe reaction vessel and filtration apparatus
  10. washwere rinsed with 100 mL tetrahydrofuran
  11. customThe combined filtrates were evaporated
  12. customto yield the crude product which
  13. customwas purified
  14. customevaporated
  15. dry with materialdried with a small amount of magnesium sulfate
  16. filtrationFiltration through a 0.2 μm PTFE
  17. filtrationfilter
  18. customrotary evaporation

출처 및 근거

ORD 기록
ord-f8cd942f8dd74280b928c62dc1b7e459
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05994317

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