Benzylamine → HCID 22012607, compound

HRID 1533121Notes

Reaction equation

HRID 1533121 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=O.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[CH2:11]([NH:18][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[N:18][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 10796Cesium carbonateHCID 1362842,6-Difluorobenzaldehyde

Product 1

HCID 22012607HCID 22012607, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A resealable tube was charged with 2,6-difluorobenzaldehyde (7.11 g, 50 mmol), benzylamine (27.3 mL, 250 mmol), cesium carbonate (19.5 g, 60 mmol), and dry toluene (170 mL). The tube was sealed and heated at 150° C. for 4 hours with rapid stirring. The reaction mixture was cooled and partitioned between ethyl acetate and 10% aqueous HCl. The organic layer was removed and the aqueous layer was extracted (2×, ethyl acetate). The combined organic extracts were washed (2×, saturated sodium bicarbonate; 2×, brine), dried (Na2SO4), filtered and concentrated under vacuum to provide the title compound (13.17 g; 83%) which was used without purification. MS (DCI/NH3) m/e 318 (M+H)+.

Workup

  1. customThe tube was sealed
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between ethyl acetate and 10% aqueous HCl
  4. customThe organic layer was removed
  5. extractionthe aqueous layer was extracted (2×, ethyl acetate)
  6. washThe combined organic extracts were washed (2×, saturated sodium bicarbonate; 2×, brine)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f425c25ed1024f79bf2c8ab1d26e99ed
Source dataset
uspto-grants-2001_03
Patent number
US06207701B1

Reaction notes

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