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

HRID 1531953Notes

Reaction equation

HRID 1531953 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].Cl.C([O-])([O-])=O.[K+].[K+].[NH:31]([CH3:33])[CH3:32]>C(Cl)(Cl)Cl>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:23])[C:9]([CH2:21][N:31]([CH3:33])[CH3:32])=[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 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-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-propanamide (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-de62202ade7243c0addaaf54efdeb66e
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

Loading…