N-bromobutanimide → 2-Amino-5-bromo-N,N-dimethyl-alpha-(3-methyl-2-thienyl)benzeneethanamine

HRID 486689Notes

Reaction equation

HRID 486689 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:13]1[S:14][CH:15]=[CH:16][C:17]=1[CH3:18])[N:10]([CH3:12])[CH3:11].[Br:19]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:19])=[CH:4][C:3]=1[CH2:8][CH:9]([C:13]1[S:14][CH:15]=[CH:16][C:17]=1[CH3:18])[N:10]([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 100611792-amino-N,N-dimethyl-alpha-(3-methyl-2-thienyl)benzeneethanamine

Product 1

HCID 224144872-Amino-5-bromo-N,N-dimethyl-alpha-(3-methyl-2-thienyl)benzeneethanamineYield 28.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6.0 g of 2-amino-N,N-dimethyl-α-(3-methyl-2-thienyl)benzeneethanamine in 30 ml of dimethylformamide, was added 5.32 g of N-bromosuccinimide in 30 ml of dimethylformamide, with stirring, and the mixture was stirred overnight at room temperature. The solution was concentrated, basified with 10% sodium hydroxide solution, and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by preparative HPLC (Water's Associates Prep LC/System 500a, silica gel, eluted with methanol, flow rate of 200 ml/min, Gow Mac model 80-800 UV detector). The appropriate fractions were collected and concentrated. The residue was dissolved in 100 ml of diethylether and filtered. The filtrate was concentrated. The residue was triturated in hexane to give 2.2 g of product, mp 96°-98° C.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. concentrationThe solution was concentrated
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC (Water's Associates Prep LC/System 500a, silica gel, eluted with methanol, flow rate of 200 ml/min, Gow Mac model 80-800 UV detector)
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated
  10. dissolutionThe residue was dissolved in 100 ml of diethylether
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated
  13. customThe residue was triturated in hexane

Sources & evidence

ORD record
ord-84683e8ed9dc4041a38f3c020ad301b7
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

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