Benzylamine → HCID 70817703, compound

HRID 2200827Notes

Reaction equation

HRID 2200827 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10]/[CH:11]=[CH:12]/[C:13]([O:15][CH3:16])=[O:14].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([NH:24][CH:11]([CH2:10][C:3]1[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=1[F:1])[CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 46849446HCID 46849446, compound

Product 1

HCID 70817703HCID 70817703, compoundYield 50.4%

Conditions

Temperature
60 °C

Procedure

In a thick-walled glass vial equipped with a magnetic stir bar was placed methyl(E)-4-(2,4,5-trifluorophenyl)-but-2-enoate (IIa) (0.5 mmol, 115 mg) and reaction system was slowly heated to 60° C. under intensive stirring. Afterwards benzylamine (0.6 mmol; 66 mL) was slowly added to (IIa) and such reaction system was vigorously stirred (800 rpm) at 70° C. for 12 hours. The reaction mixture was than extracted with tert-butyl methyl ether (20 mL), organic phase was washed with brine (20 mL) and dried over anhydrous Na2SO4. After evaporation of organic solvent under reduced pressure we obtained crude product (Ib) (85 mg, 50% yield) which was analyzed and confirmed with 1H and 13C NMR.

Workup

  1. customIn a thick-walled glass vial equipped with a magnetic stir bar
  2. extractionthan extracted with tert-butyl methyl ether (20 mL), organic phase
  3. washwas washed with brine (20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter evaporation of organic solvent under reduced pressure we

Sources & evidence

ORD record
ord-d40d8dbc92244a4a9201a1effbe194b2
Source dataset
uspto-grants-2016_06
Patent number
US09359385B2

Reaction notes

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