Methylamine → (4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamine

HRID 68615

反応式

HRID 68615 の反応式
[CH3:1][NH2:2].[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][C:12]=2[Br:19])=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][NH:2][CH3:1])=[CH:13][C:12]=2[Br:19])=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 230102233-Bromo-4-((4-methoxybenzyl)oxy)benzaldehyde

生成物 1

HCID 63045147(4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamine収率 88%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 2M methylamine in MeOH (30 mL) was added intermediate 32 (2.91 g, 9.1 mmol, 1 eq). After stirring this mixture at room temperature for 30 min, the solvent was removed and the residue was partitioned between saturated NaHCO3 and DCM (2×100 mL). The organic layer was dried (Na2SO4) and concentrated. The resultant residue was dissolved in MeOH (25 mL) and, after addition of sodium borohydride (1.0 g, 27.6 mmol, 3 eq), the mixture was stirred at room temperature for 1 h. Solvent was removed and the residue was partitioned between a Na2CO3 solution and CHCl3. The resultant organic layer was dried (Na2SO4) and concentrated in vacuo to give 2.7 g, (88%) of (4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamine (33).

後処理

  1. customthe solvent was removed
  2. customthe residue was partitioned between saturated NaHCO3 and DCM (2×100 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe resultant residue was dissolved in MeOH (25 mL)
  6. stirringthe mixture was stirred at room temperature for 1 h
  7. customSolvent was removed
  8. customthe residue was partitioned between a Na2CO3 solution and CHCl3
  9. dry with materialThe resultant organic layer was dried (Na2SO4)
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2e2bdbd81f0c4e6ea906aa73e3b13f53
出典データセット
uspto-grants-2014_09
特許番号
US08822467B2

関連ノート

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