Cyclohexanone → HCID 86603668, compound

HRID 226362Notes

Reaction equation

HRID 226362 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9][C:10]2[N:11]=[CH:12][C:13](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:14][CH:15]=2)[CH2:4]1.C(N(C(C)C)CC)(C)C.[C:32]1(=O)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.[Na].C(=O)(O)[O-].[Na+]>ClCCCl>[CH:32]1([N:3]2[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9][C:10]3[N:11]=[CH:12][C:13](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:14][CH:15]=3)[CH2:4]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

7

Reactant 5

HCID 7967CyclohexanoneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 86603669ethyl (2E)-3-{5-[(3R)-3-piperidinylamino]-2-pyrazinyl)acrylate dihydrochloride

Product 1

HCID 86603668HCID 86603668, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ethyl (2E)-3-{5-[(3R)-3-piperidinylamino]-2-pyrazinyl}acrylate dihydrochloride (300 mg) in 1,2-dichloroethane (5 mL) were added diisopropylethylamine (222 mg) and cyclohexanone (93 mg), and the mixture was stirred at ambient temperature for 5 min. To the mixture was added sodium triacetoxybrohydryde (364 mg) and stirred for 4 hrs, and resulting mixture was poured into saturated sodium bicarbonate solution, and extracted with chloroform. The organic layer was washed with water, and brine, and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified by preparative thin layer chromatography (chloroform-MeOH-10-1) to give ethyl (2E)-3-(5-{[(3R)-1-cyclohexyl-3-piperidinyl]amino}-2-pyrazinyl)acrylate (235 mg) as an amorphous powder.

Workup

  1. stirringstirred for 4 hrs
  2. customresulting mixture
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water, and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by preparative thin layer chromatography (chloroform-MeOH-10-1)

Sources & evidence

ORD record
ord-df50f85f742d4c79b928e46afc71935a
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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