Acetic Acid → HCID 81653569, compound

HRID 1436903Notes

Reaction equation

HRID 1436903 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.[CH3:17][O:18][CH2:19][CH2:20][NH2:21].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[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:21][CH2:20][CH2:19][O:18][CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 81653569HCID 81653569, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 43 ml of dichloromethane were dissolved 2.45 g of 3,5-bistrifluoromethylbenzaldehyde, 835 mg of 2-methoxyethylamine and 687 μl of acetic acid, added thereto was 3.12 g of sodium triacetoxy borohydride, and the mixture was stirred at room temperature for an hour under nitrogen atmosphere. The reaction mixture was washed with a 0.5M aqueous sodium hydroxide solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=19:1→9:1), to give 2.76 g of 3,5-bistrifluoromethylbenzyl-2-methoxyethylamine.

Workup

  1. additionadded
  2. washThe reaction mixture was washed with a 0.5M aqueous sodium hydroxide solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=19:1→9:1)

Sources & evidence

ORD record
ord-22a9d83d195548df8609edd79267491d
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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