Tert-Butylamine → HCID 53905999, compound

HRID 1756811Notes

Reaction equation

HRID 1756811 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.[C:17]1([C:23](OC)=[O:24])[CH2:22][CH2:21][CH:20]=[CH:19][CH:18]=1>C1COCC1.O>[C:1]([NH:5][C:23]([C:17]1[CH2:22][CH2:21][CH:20]=[CH:19][CH:18]=1)=[O:24])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8058HexaneHCID 12616847Methyl cyclohexa-1,3-diene-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 53905999HCID 53905999, compoundYield 33,471.199%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

t-Butylamine (2.38 g, 0.033 mmol) was dissolved in THF (20 ml), 1.6M solution of n-butyl lithium in hexane (20 ml, 0.032 mol) was added thereto at 0° C. and the mixture was stirred as it was for 40 minutes. A solution of methyl 1,3-cyclohexadiene-1-carboxylate (3 g, 0.0217 mol) synthesized in Example 12 in THF (3 ml) was added dropwise and the solution was further stirred for 30 minutes. The reaction mixture was poured in water, extracted with methylene chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (silica gel 60 g, ethyl acetate:hexane=1:5) to obtain 1,3-cyclohexadiene-1-carboxylic acid t-butylamide (1.98 g, 5 1%). This compound has the following NMR spectrum.

Workup

  1. stirringthe solution was further stirred for 30 minutes
  2. extractionextracted with methylene chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (silica gel 60 g, ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-fdd32171d13b4b9485aa3fc2a0daa886
Source dataset
uspto-grants-1995_08
Patent number
US05442062

Reaction notes

Loading…