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

HRID 65743

反応式

HRID 65743 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-455eb8b5e01d44359c3ecf6e15714f60
出典データセット
uspto-grants-1978_12
特許番号
US04128658

関連ノート

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