Diethyl Ether → N-Benzyl-N-methoxy-1-phenylmethanamine

HRID 2309752Notes

Reaction equation

HRID 2309752 reaction equation
Cl.O(N)C.[CH2:5](Br)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:13](=[O:16])([O-])[O-].[Na+].[Na+].CCO[CH2:22][CH3:23].C[N:25]([CH3:28])C=O>O>[CH3:13][O:16][N:25]([CH2:28][C:23]1[CH:22]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 17883627N-Benzyl-N-methoxy-1-phenylmethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5.11 g of methoxylaminehydrochloride, 20.87 g of benzylbromide and 25.8 g of sodium carbonate in 50 ml of dimethylformamide is heated at 85° C. for 4 hrs. The reaction mixture is treated with ether and water. The organic phase is separated and washed with water, dried (MgSO4) and evaporated under reduced pressure. Flash column chromatography of the residue affords the title compound as a clear colorless oil.

Workup

  1. customThe organic phase is separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1131ffbe0dcd48968f451b016116a15c
Source dataset
uspto-grants-1987_09
Patent number
US04696964

Reaction notes

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