Phenacyl bromide → HCID 21276526, compound

HRID 1381716Notes

Reaction equation

HRID 1381716 reaction equation
Cl.[CH3:2][NH:3][CH:4]([CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([NH:16][CH3:17])=[O:15])=[CH:8][CH:7]=1.C(N(CC)CC)C.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH3:2][N:3]([CH:4]([CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]([NH:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 21276516HCID 21276516, compound

Product 1

HCID 21276526HCID 21276526, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-methyl-2-(4-methylaminocarbonylmethoxyphenyl)-1-methylethanamine hydrochloride (2.73 g) was suspended in tetrahydrofuran (10 ml) containing triethylamine (6 ml) and a solution of α-bromoacetophenone (1.99 g) in tetrahydrofuran (10 ml) was added dropwise. After stirring overnight this solution was treated with saturated sodium carbonate solution, extracted with dichloromethane, the organic phase was dried (magnesium sulphate), filtered and evaporated to give a red oil which was used without further purification.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialthe organic phase was dried (magnesium sulphate)
  3. filtrationfiltered
  4. customevaporated
  5. customto give a red oil which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-d6086f0e5bab4a30ba3fd15725708941
Source dataset
uspto-grants-1989_02
Patent number
US04803293

Reaction notes

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