Benzaldehyde → 2-Methyl-N-(phenylmethylene)-2-propanamine

HRID 718733Notes

Reaction equation

HRID 718733 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([NH2:13])([CH3:12])([CH3:11])[CH3:10]>>[CH:1](=[N:13][C:9]([CH3:12])([CH3:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 6385Tert-Butylamine

Product 1

HCID 1112402-Methyl-N-(phenylmethylene)-2-propanamineYield 98%

Conditions

Temperature
25 °C

Procedure

530.85 g (5.00 mol) of benzaldehyde was placed into a 2000 mL-volume flask equipped with a stirrer, a thermometer and a dropping funnel. Subsequently, 367.50 g (5.02 mol) of t-butyl amine was dropped into the flask in a water bath, while maintaining the solution temperature at 25° C. After the completion of the dropping, the mixture was reacted while stirring at 25° C. for 15 hours. After the completion of the reaction, the reaction mixture was subjected to separation, and the organic layer obtained was refluxed under reduced pressure (25° C., 13.3 Pa) for 2 hours, to provide 788.91 g of N-benzylidene-t-butyl amine. (Isolation yield; 98%)

Workup

  1. customequipped with a stirrer
  2. customAfter the completion of the dropping, the mixture was reacted
  3. customAfter the completion of the reaction
  4. customthe reaction mixture was subjected to separation
  5. customthe organic layer obtained
  6. temperaturewas refluxed under reduced pressure (25° C., 13.3 Pa) for 2 hours

Sources & evidence

ORD record
ord-4e6a61839e904e18b373cc7793bf9706
Source dataset
uspto-grants-2015_11
Patent number
US09194041B2

Reaction notes

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