Triethylamine → Cyclohexaneethylamine, N-butyl-alpha,alpha-dimethyl-

HRID 530423Notes

Reaction equation

HRID 530423 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:8])[CH3:7].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>CCO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 200034Phenethylamine, N-butyl-alpha,alpha-dimethyl-

Product 1

HCID 199974Cyclohexaneethylamine, N-butyl-alpha,alpha-dimethyl-Yield 93.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Compound D-3-8 (50.0 g, 127 mmol) is combined with palladium (II) acetate (5.0 g), dppp (5.0 g) and Et3N (25.7 g, 254 mmol) in EtOH (1.0 L). The mixture is then stirred at 80° C. overnight under an atmosphere of CO at a pressure of 4 MPa. The mixture is cooled to room temperature and the solids are removed by filtration. The filtrate is concentrated under reduced pressure and the residue is purified by flash silica gel chromatography (using 20:1 petroleum ether:EtOAc) to provide compound D-3-9 (25.0 g, 62% yield).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customthe solids are removed by filtration
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue is purified by flash silica gel chromatography (using 20:1 petroleum ether:EtOAc)

Sources & evidence

ORD record
ord-3e6c26b1238946e282239fd9d7e5bd20
Source dataset
uspto-grants-2016_05
Patent number
US09353090B2

Reaction notes

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