4-(Benzyloxy)-3-bromobenzaldehyde → 3-Bromo-N-methyl-4-(phenylmethoxy)benzenemethanamine

HRID 584988ノート

反応式

HRID 584988 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[Br:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN.[C:21]([BH3-])#[N:22].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:22][CH3:21])=[CH:11][C:10]=1[Br:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 14943384-(Benzyloxy)-3-bromobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

生成物 1

HCID 171575773-Bromo-N-methyl-4-(phenylmethoxy)benzenemethanamine収率 38%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

25 g (86 mmol) of 4-benzyloxy-3-bromo-benzaldehyde, 500 ml of methanol, 29 g (430 mmol) of methylamine hydrochloride and 8 g (127 mmol) of sodium cyanoborohydride are introduced into a round-bottomed flask under a stream of nitrogen. The reaction medium is stirred for 48 hours at room temperature. The methanol is evaporated off. The residue is taken up in ethyl acetate and water and then acidified. After separation of the phases once settling has taken place, the aqueous phase is returned to basic pH with sodium hydroxide and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue is purified by chromatography on a column of silica eluted with a dichloromethane/ethanol mixture (9/1). 9.9 g (38%) of the expected product are obtained in the form of a colorless oil.

後処理

  1. customThe methanol is evaporated off
  2. customAfter separation of the phases
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by chromatography on a column of silica
  8. washeluted with a dichloromethane/ethanol mixture (9/1)

出典と根拠

ORDレコード
ord-53cb573b34a348fe85b54a1bfdd811d1
出典データセット
uspto-grants-2005_08
特許番号
US06927228B2

反応ノート

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