Aniline → N-Phenyl-2-benzyloxyethylamine

HRID 1629595Notes

Reaction equation

HRID 1629595 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.Br[CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:20]([O:19][CH2:18][CH2:17][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 79372,6-LutidineHCID 73833Benzene, ((2-bromoethoxy)methyl)-

Product 1

HCID 571665N-Phenyl-2-benzyloxyethylamineYield 45.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In a round bottom flask aniline (2.0 g, 21.5 mmol, 2.0 mL), 2,6-lutidine (2.30 g, 21.5 mmol) and benzyl 2-bromoethyl ether (4.6 g, 21.5 mmol, 3.4 mL) were combined in DMF (10 mL) and stirred at 100° C. overnight. The reaction was allowed to cool and then diluted with ethyl acetate (50 mL). This was washed with water (3×20 nit) and the organics were dried and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (0-50% B, 100 g, 19.5 CV, 85 mL/min) to afford 2.22 g (37%) of (2-benzyloxy-ethyl)-phenyl-amine (21) as a yellow oil. The structure was confirmed by 13C NMR (75 MHz, CDCl3) δC 43.6, 68.6, 73.2, 113.1, 117.5, 127.5, 127.7, 128.4, 129.1, 138.2, 148.1

Workup

  1. temperatureto cool
  2. washThis was washed with water (3×20 nit)
  3. customthe organics were dried
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with petrol (A) and ethyl acetate (B) (0-50% B, 100 g, 19.5 CV, 85 mL/min)

Sources & evidence

ORD record
ord-c345976f805243d19dec7a2708aadf6c
Source dataset
uspto-grants-2014_07
Patent number
US08790619B2

Reaction notes

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