Water → 1-(6-Bromo-1H-indol-3-yl)-N,N-dimethylmethanamine

反応式

[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[Cl-].C[CH:13]=[N+:14]=[CH:15]C.O.[OH-].[Na+].[CH2:20](Cl)Cl>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:13][N:14]([CH3:15])[CH3:20])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

参加物

反応物 5

HCID 962Water

HCID 6344Dichloromethane

HCID 14798Sodium Hydroxide

HCID 6764936-Bromoindole

HCID 21873455N,N-dimethylmethylene ammonium chloride

生成物 1

HCID 133840941-(6-Bromo-1H-indol-3-yl)-N,N-dimethylmethanamine収率 100%

実験手順

To a solution of 6-bromoindole (7.18 g, 36.6 mmol) in CH2Cl2 (140 mL) was added N,N-dimethylmethylene ammonium chloride (5.48 g, 58.6 mmol, 1.60 eq.) in one portion and the resultant mixture was stirred at rt for 2 h under N2. Water (150 mL) and 1M NaOH (62 mL, 62 mmol) were added, and the reaction mixture was extracted with EtOAc (300 mL). The organic layer was washed with aqueous saturated NaCl and dried (MgSO4). The solvent was removed in vacuo to give 9.29 g (100%) of the title compound.