Acetic Acid → HCID 11171028, compound

HRID 658080Notes

Reaction equation

HRID 658080 reaction equation
[CH:1]1([CH:7]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH2:10]([NH:12]CC)[CH3:11].C(O)(=O)C.[OH-].[Na+]>C(Cl)Cl>[CH:1]1([CH2:7][NH:12][CH2:10][CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 16275CyclohexanecarboxaldehydeHCID 10197650Diethylammonium chloride

Product 1

HCID 11171028HCID 11171028, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclohexanecarboxaldehyde (38 g), diethylamine hydrochloride (55 g) and acetic acid (29 ml) are dissolved in methylene chloride (500 ml) and thereto is added triacetoxy sodium borohydride (71.8 g) at room temperature and the mixture is stirred at room temperature overnight. To the reaction solution are added a 2N-aqueous sodium hydroxide solution and methylene chloride, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and the mixture is concentrated under reduced pressure to give cyclohexylmethyl-ethyl-amine (40.1 g) as a crude product. MS (m/z): 142 [M+H]+

Workup

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationthe mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-b84976d3e48c46f0a564e7d4d72428b0
Source dataset
uspto-grants-2011_12
Patent number
US08076364B2

Reaction notes

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