N-Methylbenzylamine → HCID 66744778, compound

HRID 1259305Notes

Reaction equation

HRID 1259305 reaction equation
[H-].[Na+].[CH2:3]1[CH2:7][O:6][CH2:5][CH2:4]1.[CH3:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OCCBr)C>C(OCC)(=O)C.O>[CH2:5]([O:6][CH2:7][CH2:3][N:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:8])[CH3:4]

Participants

7

Reactant 4

HCID 7669N-MethylbenzylamineHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl ether

Product 1

HCID 66744778HCID 66744778, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Process 1) NaH (washed with hexane in advance, 8.78 g, 0.305×1.2 mol) was added to a dry THF (300 mL) solution of N-methylbenzylamine (39 mL, 0.305 mol) under an argon atmosphere at room temperature. After stirring at room temperature for 30 minutes, a dry THF (100 mL) solution of bromoethyl ethyl ether (51 mL, 0.305×1.5 mol) was added dropwise, and further heated under reflux under an argon atmosphere for 24 hours. After cooling to room temperature, water (350 mL) was carefully added for dissolution of insoluble materials, followed by adding ethyl acetate (350 mL). The organic layer was separated, further washed with brine (200 mL) and then concentrated to dryness. Since insoluble materials precipitated in the residual fraction, they were filtered off and washed with ethyl acetate, and the filtrate was again concentrated to dryness. The residue was purified by vacuum distillation (fraction at 1.0 to 1.1 kpa and 95° C. to 110° C. collected), and BnEO (49.73 g, 0.257 mol, 84%) was obtained as a colorless transparent liquid.

Workup

  1. temperaturefurther heated
  2. temperatureunder reflux under an argon atmosphere for 24 hours
  3. temperatureAfter cooling to room temperature
  4. customThe organic layer was separated
  5. washfurther washed with brine (200 mL)
  6. concentrationconcentrated to dryness
  7. customSince insoluble materials precipitated in the residual fraction, they
  8. filtrationwere filtered off
  9. washwashed with ethyl acetate
  10. concentrationthe filtrate was again concentrated to dryness
  11. distillationThe residue was purified by vacuum distillation (fraction at 1.0 to 1.1 kpa and 95° C. to 110° C. collected)
  12. customBnEO (49.73 g, 0.257 mol, 84%) was obtained as a colorless transparent liquid

Sources & evidence

ORD record
ord-4f4c0d43b2884d8b8f7e9fc65f9f5a8c
Source dataset
uspto-grants-2013_06
Patent number
US08466287B2

Reaction notes

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