Diethyl Ether → 2-(4-BROMOPHENYL)-N,N-DIMETHYLETHANAMINE

HRID 1744093Notes

Reaction equation

HRID 1744093 reaction equation
CCOCC.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=O)=[CH:9][CH:8]=1.CCOCC.C1COCC1.[OH-].[Na+]>O>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][N:16]([CH3:17])[CH3:18])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 46315952-(4-bromophenyl)-N,N-dimethylacetamideHCID 21868444Ether tetrahydrofuran

Product 1

HCID 107518022-(4-BROMOPHENYL)-N,N-DIMETHYLETHANAMINEYield 12.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of LiAlH4in ether (5 mL) was added a solution of 2-(4-bromophenyl)-N,N-dimethylacetamide (1.1 g, 4.5 mmol) in 5:1 ether/THF (12 mL), giving a small exotherm. The mixture was stirred at room temperature for 3 h, refluxed overnight then cooled to 0° C. Water (0.5 mL) was added dropwise and the mixture stirred vigourously for 3 h, then poured into 1 M NaOH and extracted with ether. The organic phase was washed with brine and dried over MgSO4. Purification by flash chromatography (4% to 8% MeOH/dichloromethane+0.5% ammonium hydroxide) provided 132 mg of 2-(4-bromophenyl)-N,N-dimethylethanamine.

Workup

  1. customgiving a small exotherm
  2. temperaturerefluxed overnight
  3. temperaturethen cooled to 0° C
  4. stirringthe mixture stirred vigourously for 3 h
  5. extractionextracted with ether
  6. washThe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. customPurification by flash chromatography (4% to 8% MeOH/dichloromethane+0.5% ammonium hydroxide)

Sources & evidence

ORD record
ord-61ea48b0fc334f87ade1929632ac5652
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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