2-Chloro-N,N-dimethylethylamine → HCID 86639067, compound

HRID 1684933Notes

Reaction equation

HRID 1684933 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[CH:2].Cl[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])#[CH:2]

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 10796Cesium carbonateHCID 139144m-Ethynylphenol

Product 1

HCID 86639067HCID 86639067, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

3-Ethynylphenol (1.18 g, 10 mmol), 2-chloro-N,N-dimethylethanamine (1.44 g, 10 mmol), Cesium carbonate (7.0 g, 21 mmol) was dissolved in dimethyl formamide (20 mL) and the mixture was heated to 65° C. for 1 h. The mixture was cooled to RT and the partitioned between water and dichloromethane. The organic layer was separated, washed with 2N NaOH and then extracted with 1N HCl. The HCl solution was then neutralized with aqueous NaOH and extracted with dichloromethane. The organic layer was dried and concentrated to afford 2-(3-ethynylphenoxy)-N,N-dimethylethanamine (0.6 g) as an oil. LC/MS; (M+H)+=190.

Workup

  1. temperatureThe mixture was cooled to RT
  2. customthe partitioned between water and dichloromethane
  3. customThe organic layer was separated
  4. washwashed with 2N NaOH
  5. extractionextracted with 1N HCl
  6. extractionextracted with dichloromethane
  7. customThe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a77cee165f1b4a36bfab1a79e5c47ec1
Source dataset
uspto-grants-2012_04
Patent number
US08148361B2

Reaction notes

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