N-bromobutanimide → HCID 22414392, compound

HRID 486673Notes

Reaction equation

HRID 486673 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[CH:16]=[CH:15][S:14][C:13]=1[CH3:17])[NH:10][CH3:11].[Br:18]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:18])=[CH:4][C:3]=1[CH2:8][CH:9]([C:12]1[CH:16]=[CH:15][S:14][C:13]=1[CH3:17])[NH:10][CH3:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22414442HCID 22414442, compound

Product 1

HCID 22414392HCID 22414392, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 3.0 g of 2-amino-N-methyl-α-(2-methyl-3-thienyl)benzeneethanamine in 50 ml of N,N-dimethylformamide was treated with a solution of 2.6 g of N-bromosuccinimide in 50 ml of N,N-dimethylformamide and allowed to stand overnight at room temperature. Evaporation of the volatiles afforded an oil which was purified by HPLC (Water's Associates Prep LC/System 500, silica gel, elution with methanol). The resultant oil was dissolved in diethyl ether, filtered and concentrated. Trituration with diethyl ether afforded 1.2 g of 2-amino-5-bromo-N-methyl-α-(2-methyl-3-thienyl)benzeneethanamine, mp 72.5°-74° C.

Workup

  1. customEvaporation of the volatiles
  2. customafforded an oil which
  3. customwas purified by HPLC (Water's Associates Prep LC/System 500, silica gel, elution with methanol)
  4. dissolutionThe resultant oil was dissolved in diethyl ether
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e916b056432e4e769143fdcdc88d9514
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

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