Benzylamine → N-Benzyl-2-phenylacrylamide

HRID 1736646Notes

Reaction equation

HRID 1736646 reaction equation
[C:1]([OH:11])(=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1.CCOCC>[C:4]1([C:2](=[CH2:3])[C:1]([NH:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:11])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 68114Atropic acid

Product 1

HCID 54041249N-Benzyl-2-phenylacrylamideYield 44.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of atropic acid (10.3 g, 69.5 mmol) in dry tetrahydrofuran (100 ml) was treated under nitrogen with N-methylmorpholine (7.7 ml, 70.0 mmol), cooled to -10°, treated dropwise with iso-butylchloroformate (9 ml, 69.4 mmol), treated dropwise with benzylamine (7.6 ml, 69.6 mmol), warmed to room temperature over 1 hour, filtered and evaporated in vacuo to give a yellow oil which was dissolved in ether (100 ml). The solution was washed with 0.1N--HCl (200 ml), brine (100 ml), 0.1N--NaOH (100 ml) and brine (100 ml) , dried (MgSO4), and evaporated in vacuo to give a yellow liquid. Purification by chromatography (silica; di-iso-propyl ether) gave the product as white crystals (7.3g), m.p. 84°-86° (from di-iso-propyl ether).

Workup

  1. temperaturecooled to -10°
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customto give a yellow oil which
  5. washThe solution was washed with 0.1N
  6. dry with materialHCl (200 ml), brine (100 ml), 0.1N--NaOH (100 ml) and brine (100 ml) , dried (MgSO4)
  7. customevaporated in vacuo
  8. customto give a yellow liquid
  9. customPurification by chromatography (silica; di-iso-propyl ether)

Sources & evidence

ORD record
ord-7ce95e7efe834c38a70b0c29005e36d8
Source dataset
uspto-grants-1996_07
Patent number
US05541326

Reaction notes

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