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

HRID 2215746Notes

Reaction equation

HRID 2215746 reaction equation
[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

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 6764936-BromoindoleHCID 21873455N,N-dimethylmethylene ammonium chloride

Product 1

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

Procedure

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.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc (300 mL)
  2. washThe organic layer was washed with aqueous saturated NaCl
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a0015afd2ccc495999c2956388d899a0
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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