Iodine → N-(2-(2-benzyloxyphenyl)ethyl)-N-methylamine

HRID 366154ノート

反応式

HRID 366154 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([NH:18][CH3:19])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].II.CO>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][NH:18][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 807IodineHCID 887MethanolHCID 4311764Sodium borohydrideHCID 105871262-(2-benzyloxyphenyl)-N-methylacetamide

生成物 1

HCID 21712301N-(2-(2-benzyloxyphenyl)ethyl)-N-methylamine収率 49.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

At 0° C., a solution of 2-(2-benzyloxyphenyl)-N-methylacetamide (9.39 g, 36.8 mmol) in tetrahydroufran (150 ml) was added dropwise to a suspension of sodium borohydride (1.67 g, 44.12 mmol) in tetrahydrofuran (100 ml). After the addition was finished, a solution of iodine (4.67 g, 18.39 mmol) in tetrahydrofuran (200 ml) was added dropwise. The solution was warmed to reflux for 16 h. It was cooled to 0° C. Methanol (200 ml) was added dropwise. The solvent was removed in vacuo. The residue was dissolved in an aqueous 20% sodium hydroxide solution (200 ml) and tert-butyl methyl ether (200 ml). The phases were separated. The aqueous phase was extracted with tert-butyl methyl ether (3×75 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (400 g), using dichloromethane/methanol/25% aqueous ammonia as eluent (100:10:1), to give 4.38 g of N-(2-(2-benzyloxyphenyl)ethyl)-N-methylamine.

後処理

  1. additionAfter the addition
  2. temperatureThe solution was warmed
  3. temperatureto reflux for 16 h
  4. customThe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in an aqueous 20% sodium hydroxide solution (200 ml) and tert-butyl methyl ether (200 ml)
  6. customThe phases were separated
  7. extractionThe aqueous phase was extracted with tert-butyl methyl ether (3×75 ml)
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. customThe solvent was removed in vacuo
  10. customThe crude product was purified by flash chromatography on silica (400 g)

出典と根拠

ORDレコード
ord-406add055946494cbb2324726b3cdbf5
出典データセット
uspto-grants-2000_10
特許番号
US06127354

反応ノート

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