Ethylamine → N-ethyl-N-(2-(phenoxy)benzyl)amine

HRID 355769Notes

Reaction equation

HRID 355769 reaction equation
[CH2:1]([NH2:3])[CH3:2].[C:4]1([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17]Br)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.C1COCC1>[CH2:1]([NH:3][CH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 226754691-(Bromomethyl)-2-phenoxybenzene

Product 1

HCID 22675571N-ethyl-N-(2-(phenoxy)benzyl)amineYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethylamine (70% solution, 5.2 ml, 80 mmol) was diluted with water (5.2 ml). A solution of 2-bromomethylphenyl phenyl ether (5.0 g, 19.02 mmol) in THF (25 ml) was added dropwise and the reaction stirred at ambient temperature for 2 hours. The volatile components were removed at reduced pressure, aqueous sodium hydroxide (1N, 20 ml) was added and the aqueous solution extracted with dichloromethane (2×). The organic layers were dried (MgSO4), evaporated and purified by chromatography (eluant: CH2 Cl2 /EtOAc/MeOH) to give N-ethyl-N-(2-(phenoxy)benzyl)amine as a yellow solid (2.2 g, 51%).

Workup

  1. customThe volatile components were removed at reduced pressure, aqueous sodium hydroxide (1N, 20 ml)
  2. additionwas added
  3. extractionthe aqueous solution extracted with dichloromethane (2×)
  4. dry with materialThe organic layers were dried (MgSO4)
  5. customevaporated
  6. custompurified by chromatography (eluant: CH2 Cl2 /EtOAc/MeOH)

Sources & evidence

ORD record
ord-2f418be54eed404683d12424a85aae4c
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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