Water → N-[(3,5-dichlorophenyl)methyl]-2,2-bis(methyloxy)ethanamine

HRID 493439Notes

Reaction equation

HRID 493439 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][NH2:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Br[CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 457602Benzenemethanamine, 3,5-dichloro-

Product 1

HCID 60816340N-[(3,5-dichlorophenyl)methyl]-2,2-bis(methyloxy)ethanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [(3,5-dichlorophenyl)methyl]amine (100 mg), 2-bromo-1, 1bis(methyloxy)ethane (123 μL) and K2CO3 (95 mg) in anhydrous DMF (2 mL) was processed by microwave irradiation at 150° C. for 10 min (3 cycles). The mixture was allowed to cool to rt, water was added and mixture extracted three times with AcOEt, the organic phases collected, washed with brine, dried and evaporated under vacuum to give a crude which was purified by flash cromathography eluting with CH:AcOEt=9:1 to 85:15 to afford the title compound (120 mg) as a colourless oil.

Workup

  1. customwas processed by microwave irradiation at 150° C. for 10 min (3 cycles)
  2. extractionmixture extracted three times with AcOEt
  3. customthe organic phases collected
  4. washwashed with brine
  5. customdried
  6. customevaporated under vacuum
  7. customto give a crude which
  8. customwas purified by flash cromathography
  9. washeluting with CH

Sources & evidence

ORD record
ord-4e094841c39d41218c410f44c7656e24
Source dataset
uspto-grants-2009_05
Patent number
US07534893B2

Reaction notes

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