Ethylamine → N-(3,5-bistrifluoromethylbenzyl)-N-ethylamine

HRID 1436908Notes

Reaction equation

HRID 1436908 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[CH2:17]([NH2:19])[CH3:18].O1CCCC1.[BH4-].[Na+]>CO>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6][NH:19][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 59735055N-(3,5-bistrifluoromethylbenzyl)-N-ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 20 ml of methanol was dissolved 24.5 g of 3,5-bistrifluoromethylbenzaldehyde, and under ice-cooling, added thereto was 60 ml of ethylamine (a 2M tetrahydrofuran solution). Subsequently, 4.38 g of sodium borohydride was slowly added thereto, and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added distilled water and concentrated under reduced pressure. The residue was extracted with dichloromethane, and the organic layer was dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→chloroform:methanol=9:1), to give 6.35 g of N-(3,5-bistrifluoromethylbenzyl)-N-ethylamine as shown in Table 135 below.

Workup

  1. temperatureunder ice-cooling
  2. additionadded
  3. additionTo the reaction mixture was added
  4. distillationdistilled water
  5. concentrationconcentrated under reduced pressure
  6. extractionThe residue was extracted with dichloromethane
  7. customthe organic layer was dried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-2dc5eb58397d403f947fcb526c49a766
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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