Acetic Acid → Benzyl 4-[4-[(3-chloropyrazin-2-yl)methylcarbamoyl]cyclohexyl]piperazine-1-carboxylate

HRID 245658Notes

Reaction equation

HRID 245658 reaction equation
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([CH:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1.C(O)(=O)C.[N:23]1([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C([BH3-])#N.[Na+]>ClCCl>[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([CH:12]2[CH2:17][CH2:16][CH:15]([N:26]3[CH2:25][CH2:24][N:23]([C:29]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])[CH2:28][CH2:27]3)[CH2:14][CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 643495Benzyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 86674630N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamide

Product 1

HCID 86674631Benzyl 4-[4-[(3-chloropyrazin-2-yl)methylcarbamoyl]cyclohexyl]piperazine-1-carboxylateYield 134.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamide (3.7 mmol, 1 g) was dissolved in dichloromethane (10 mL) and acetic acid (0.1 mL) was added. To this solution benzyl 1-piperazinecarboxylate (11.2 mmol, 2.16 mL) and sodium cyanoborohydride (7.47 mmol, 0.47 g) were added subsequently. The mixture was stirred overnight at room temperature. Reaction was quenched with an aqueous sodium hydrogencarbonate solution and extracted twice with dichloromethane. The combined organic layers were dried over phase separation filter, concentrated under reduced pressure and purified using column chromatography (silica gel; dichloromethane/methanol) to yield 2.35 g of the title compound as a mixture of cis and trans isomers which was used in the next step without further purification.

Workup

  1. customReaction
  2. customwas quenched with an aqueous sodium hydrogencarbonate solution
  3. extractionextracted twice with dichloromethane
  4. customThe combined organic layers were dried over phase separation
  5. filtrationfilter
  6. concentrationconcentrated under reduced pressure
  7. custompurified

Sources & evidence

ORD record
ord-610880f09088408884e26a553760192c
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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