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

HRID 127308

反応式

HRID 127308 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, 5 N 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.

後処理

  1. customThe solution was evaporated
  2. temperaturethe oily residue heated at 98°-100° for 10 mins
  3. addition5 N 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-c0326498108841bcbece3248ebb4d258
出典データセット
uspto-grants-1981_03
特許番号
US04255440

関連ノート

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