Methanesulfonic Acid → 2-[[5-(Dimethylamino)methyl-2-furanyl]methoxy]ethanamine

HRID 65743

반응식

HRID 65743 반응식
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][OH:11])=[CH:7][CH:6]=1)[CH3:3].[CH2:12]1[NH:14][CH2:13]1.CS(O)(=O)=O>O1CCCC1>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][O:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:1]

참가 물질

5

반응물 3

HCID 6395Methanesulfonic AcidHCID 9033AziridineHCID 849065-((Dimethylamino)methyl)-2-furanmethanol

생성물 1

HCID 202133122-[[5-(Dimethylamino)methyl-2-furanyl]methoxy]ethanamine수율 2.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 5-(dimethylamino)methyl-2-furanmethanol (6.2 g) and ethylene imine (2.82 g) in dry tetrahydrofuran was added a solution of methanesulphonic acid (11.6 g) in tetrahydrofuran (40 ml). The solution was evaporated and the oily residue heated at 98°-100° for 10 mins. After 18 hr, 5N sodium hydroxide (60 ml) was added and the solution evaporated to dryness. Anhydrous sodium sulphate and ethyl acetate (150 ml) were added and after 2 hr the suspension was filtered, treated with decolourising charcoal and evaporated. The resulting oil was chromatographed on silica, firstly with methanol-ammonia 0.88 79:1, and the eluate discarded, and secondly with methanol-ammonia 0.88 19:1. This eluate was evaporated to give an oil from which the bisoxalate salt of 2-[[5-(dimethylamino)methyl-2-furanyl]methoxy]ethanamine (from ethanol) 0.2 g, m.p. 125°-128°, was obtained. Route (ii)

후처리

  1. customThe solution was evaporated
  2. temperaturethe oily residue heated at 98°-100° for 10 mins
  3. addition5N sodium hydroxide (60 ml) was added
  4. customthe solution evaporated to dryness
  5. additionAnhydrous sodium sulphate and ethyl acetate (150 ml) were added and after 2 hr the suspension
  6. filtrationwas filtered
  7. additiontreated with decolourising charcoal
  8. customevaporated
  9. customThe resulting oil was chromatographed on silica, firstly with methanol-ammonia 0.88 79:1
  10. customThis eluate was evaporated

출처 및 근거

ORD 기록
ord-455eb8b5e01d44359c3ecf6e15714f60
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04128658

연결된 노트

불러오는 중…