Ethyl Bromide → HCID 69419942, compound

HRID 456431Notes

Reaction equation

HRID 456431 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C@H:6]([NH2:8])[CH3:7].Br[CH2:14][CH3:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C@H:6]([NH:8][CH2:14][CH3:15])[CH3:7]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 28804183HCID 28804183, compound

Product 1

HCID 69419942HCID 69419942, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-2-(2-bromophenoxy)-1-methylethylamine, (Preparation 1A, Step 2) (1.68 g, 7.3 mmol) was dissolved in DMF (16 ml). The mixture was stirred with bromoethane (3.18 ml, 43 mmol) and K2CO3 (7.60 g, 55 mmoles) at r.t. under N2 for about 3 days. The mixture was concentrated, dissolved in EtOAc, washed with water and brine, dried over Na2SO4, and filtered. Solvent was removed and the residue was purified by flash chromatography (silica gel, 5% 2M NH3 in MeOH/CH2Cl2) to give about 2.08 g of a mixture of diethyl and monoethyl amine compounds with the mono ethyl as the minor product.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customSolvent was removed
  7. customthe residue was purified by flash chromatography (silica gel, 5% 2M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cf3df34387d6463e929e63b7f473ae31
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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