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1-Methylpiperazine → HCID 178480930, compound

HRID 245674
Notes
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Reaction equation

HRID 245674 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.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>ClCCl.C(O)(=O)C>[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[CH2:14][CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 86674630N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamide

Product 1

HCID 178480930HCID 178480930, compound

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Solvent
HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamide (40.7 mmol, 10.9 g) in dichloromethane (145 ml) and acetic acid (1.450 ml) at room temperature was added 1-methylpiperazine (52.9 mmol, 5.87 ml, 5.30 g) and sodium cyanoborohydride (81 mmol, 5.12 g). After 16 hours at room temperature dichloromethane and an aqueous saturated sodium hydrogencarbonate solution (15 mL) were added and the organic layer was separated. This organic layer was washed with brine. The aqueous layers were washed with dichloromethane twice and the combined organic extracts dried (sodium sulfate). Concentration in vacuo gave the crude product (mixture of cis and trans), which was purified using column chromatography (silica gel; dichloromethane/methanol gradient (0 to 20% methanol) to afford the cis isomer (275 mg), the trans isomer (2.5 g) and a mixture of cis and trans isomers (5.5 g).

Workup

  1. customthe organic layer was separated
  2. washThis organic layer was washed with brine
  3. washThe aqueous layers were washed with dichloromethane twice
  4. dry with materialthe combined organic extracts dried (sodium sulfate)
  5. concentrationConcentration in vacuo
  6. customgave the crude product (mixture of cis and trans), which
  7. customwas purified
  8. customdichloromethane/methanol gradient (0 to 20% methanol) to afford the cis isomer (275 mg)
  9. additionthe trans isomer (2.5 g) and a mixture of cis and trans isomers (5.5 g)

Sources & evidence

ORD record
ord-a6ec05827bec46c78dbd0307aae05faf
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658794B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes