Benzylamine → HCID 22011791, compound

HRID 1532961Notes

Reaction equation

HRID 1532961 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:11]([NH:18][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 788712-(2-(2-Chloroethoxy)ethoxy)ethanol

Product 1

HCID 22011791HCID 22011791, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

2-[2-(2-Chloroethoxy)ethoxy]ethanol 31 (9.273 g, 55 mmol) and benzylamine (26.3 mL, 240 mmol) were dissolved in absolute acetonitrile (150 mL) whereupon potassium carbonate (25.0 g, 180 mmol) was added. The suspension was heated at reflux with vigorous stirring under an argon atmosphere for 18 hours. The suspension was allowed to cool to room temperature, diluted with acetonitrile (100 mL) and filtered through a Celite™ pad. The acetonitrile was removed under reduced pressure and the unreacted benzylamine distilled from the concentrated pale greenish oil under high vacuum (90° C., 5 torr). The resulting viscous oil (14.2 g) was purified by flash chromatography using 13% methanol in dichloromethane as the eluent. Fractions contained the desired product (Rf=0.45) were combined, solvent removed under reduced pressure, and the residue dried in vacuo to yield the title compound as a viscous oil (10.1 g, 77%). CIMS (MH+): m/e 240. 1H-NMR (CDCl3): δ 7.31 (m, 5H, phenyl), 3.79 (s, 2H, CH2-Ph), 3.70-3.61 (m, 12 H, OCH2CH2O). 13C-NMR (CDCl3): δ 140.3, 129.0, 128.8, 127.6, 73.3, 70.9, 70.8, 70.7, 62.0, 54.4, 49.0.

Workup

  1. additionwas added
  2. temperatureThe suspension was heated
  3. temperatureat reflux
  4. filtrationfiltered through a Celite™ pad
  5. customThe acetonitrile was removed under reduced pressure
  6. distillationthe unreacted benzylamine distilled from the concentrated pale greenish oil under high vacuum (90° C., 5 torr)
  7. customThe resulting viscous oil (14.2 g) was purified by flash chromatography
  8. customsolvent removed under reduced pressure
  9. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-1bed92e42b8940188750e0b77f4b12d7
Source dataset
uspto-grants-2001_03
Patent number
US06207660B1

Reaction notes

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