Hexanal → N-(tert-butyl)-N-hexylideneamine

HRID 76244

Reaction equation

HRID 76244 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].[CH:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>C(Cl)Cl>[C:1]([N:5]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6184HexanalHCID 6385Tert-ButylamineHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 11829679N-(tert-butyl)-N-hexylideneamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To t-butyl amine (5.25 mL, 50.0 mmol) and MgSO4 (2 g) in CH2Cl2 (10 mL) at room temperature was added slowly hexanal (6.0 mL, 50 mmol) under N2 at room temperature. The reaction became exothermic halfway through the addition so an ice bath was briefly used to control the reaction rate and avoid boiling off the solvent or amine. After the addition was complete, the reaction was stirred at room temperature for 2 h, filtered through celite under a stream of N2 and washed with 20 mL dry CH2Cl2. The solvent was evaporated to give a pale yellow liquid. 1H NMR (300 MHz, CDCl3) δ 0.87-0.91 (m, 3H), 1.17 (s, 9H), 1.25-1.35 (m, 4H), 1.45-1.55 (m, 2H), 2.23 (m, 2H), 7.59 (t, 1H).

Workup

  1. additionthrough the addition so an ice bath
  2. additionAfter the addition
  3. filtrationfiltered through celite under a stream of N2
  4. washwashed with 20 mL dry CH2Cl2
  5. customThe solvent was evaporated
  6. customto give a pale yellow liquid

Sources & evidence

ORD record
ord-2881d6ca74c5407e8f5f4edf29f409b2
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Linked notes

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