Dimethylamine, hydrochloride → N-(1-Acetyl-5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1107943Notes

Reaction equation

HRID 1107943 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:23])[C:9]([CH2:21]Cl)=[C:10]([CH3:20])[C:11]=2[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[NH:24]([CH3:26])[CH3:25].Cl.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:23])[C:9]([CH2:21][N:24]([CH3:26])[CH3:25])=[C:10]([CH3:20])[C:11]=2[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 15895572N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 22247311N-(1-Acetyl-5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamideYield 34.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide (2.0 g) was dissolved in CHCl3 (40 ml) and (CH3)2NH.HCl (3.5 g) and K2CO3 (11.8 g) were added, which was followed by stirring at room temperature for 4 hr. CHCl3 (300 ml) was added, and the mixture was washed successively with 2N-hydrochloric acid, 2N aqueous NaOH and saturated brine, and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=10/1-1/1) to give 700 mg of N-(1-acetyl-5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide.

Workup

  1. washthe mixture was washed successively with 2N-hydrochloric acid, 2N aqueous NaOH and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customCHCl3 was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=10/1-1/1)

Sources & evidence

ORD record
ord-d96a158f2fb1416886ac9a2b2eb716eb
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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