Triethylamine → HCID 57672929, compound

HRID 1627450Notes

Reaction equation

HRID 1627450 reaction equation
[C:1]1([CH2:7][O:8][C:9]([C:11]2([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:19].C(N(CC)CC)C.[NH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][C:41]1=[O:46]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]1([CH2:7][O:8][C:9]([C:11]2([NH:17][C:18]([N:40]3[CH2:45][CH2:44][CH2:43][CH2:42][C:41]3=[O:46])=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 126652-PiperidoneHCID 90495Di-tert-butyl dicarbonateHCID 15176238Benzyl 1-aminocyclohexanecarboxylate

Product 1

HCID 57672929HCID 57672929, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 183 mg (1.5 mmol) of N,N-dimethylaminopyridine and 3.50 g (15 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester in toluene was added to a solution of 3.27 g (15 mmol) of di-t-butyl dicarbonate in 60 ml of toluene, and the mixture was stirred at room temperature for 30 minutes. Thereafter, 3.04 g (30 mmol) of triethylamine, 1.83 g (15 mmol) of N,N-dimethylaminopyridine and 1.56 g (15.8 mmol) of 2-piperidone were added to the reaction mixture, and the mixture was heated under reflux overnight. Ethyl acetate was added to the reaction solution, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel chromatography to obtain 4.10 g (76%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. washthe mixture was successively washed with water
  4. dry with materialby drying with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4fd421f2b70848608b7829510066a8dc
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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