Methylamine → HCID 68674592, compound

HRID 1927682Notes

Reaction equation

HRID 1927682 reaction equation
[CH3:1][NH2:2].C1COCC1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH:19][CH2:20][C:21](=O)[CH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][CH3:25])=O)=[CH:11][CH:10]=1>C(O)(=O)C.O>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2[N:2]([CH3:1])[C:21]([CH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][CH3:25])=[CH:20][N:19]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 6329Methylamine2×HCID 8028TetrahydrofuranHCID 68673705HCID 68673705, compound

Product 1

HCID 68674592HCID 68674592, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

Acetic acid (1.08 mL, 18.9 mmol) and 2M methylamine in THF (1.09 mL, 2.2 mmol) were added to a solution of 3-(4-bromophenyl)-N-(4,4-dimethyl-2-oxohexyl)propanamide in xylenes (20 mL). The solution was stirred at reflux with azeotropic removal of water for 1 h. Another batch of acetic acid and methylamine were added and stirring was continued at reflux for another 4 h. After cooling to rt, the solution was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give 2-[2-(4-bromophenyl)ethyl]-5-(2,2-dimethylbutyl)-1-methyl-1H-imidazole.

Workup

  1. stirringstirring
  2. temperatureat reflux for another 4 h
  3. washthe solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-693dab4f6f794d2ebcbf0445fa19ff87
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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