Benzaldehyde → HCID 178448941, compound

HRID 529505Notes

Reaction equation

HRID 529505 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH:3]=[CH2:4].[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CO>[CH:6](=[N:5]/[CH2:1][CH2:2][CH:3]=[CH2:4])\[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 4437323-Buten-1-amine

Product 1

HCID 178448941HCID 178448941, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of but-3-en-1-amine (580 mg, 8.16 mmol) in anhydrous MeOH (20 mL) was added a dozen molecular sieve beads. Benzaldehyde (865 mg, 8.16 mmol) was added dropwise. The mixture was stirred at rt for 18 hr, The reaction mixture was filtered, and the filtrate was concentrated to dryness to give (E)-N-benzylidenebut-3-en-1-amine (1.30 gm, 8.16 mmol, 99% yield) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 8.28 (s, 1H), 7.76-7.70 (m, 2H), 7.41 (dd, J=5.0, 1.8 Hz, 3H), 5.86 (ddt, J=17.1, 10.2, 6.8 Hz, 1H), 5.20-4.97 (m, 2H), 3.69 (td, J=7.2, 1.2 Hz, 2H), 2.47 (td, J=7.1, 1.1 Hz, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-0ddfb039abca416284bcab3af89431df
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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