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

HRID 530421Notes

Reaction equation

HRID 530421 reaction equation
[CH3:1][CH2:2][CH2:3][NH:4][C:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:7])[CH3:6].CCN(CC)CC.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>C1COCC1.O>[CH3:1][CH2:2][CH2:3][NH:4][C:5]([CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 200033Phenethylamine, alpha,alpha-dimethyl-N-propyl-

Product 1

HCID 199973Cyclohexaneethylamine, alpha,alpha-dimethyl-N-propyl-Yield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound D-3-6 (195.0 g, 799 mmol) in THF (1.0 L) and H2O (1.0 L) is added Et3N (242.0 g, 2.4 mol) and Boc2O (174.0 g, 799 mmol). The resulting mixture is stirred at room temperature overnight, then extracted with EtOAc. The combined organic phases are washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by silica gel chromatography (using 10:1 petroleum ether:EtOAc) to provide compound D-3-7 (100.0 g, 56% yield over 4 steps).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by silica gel chromatography (using 10:1 petroleum ether:EtOAc)

Sources & evidence

ORD record
ord-5fd7d2743868464d9af5da354ff7324a
Source dataset
uspto-grants-2016_05
Patent number
US09353090B2

Reaction notes

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