N-Piperidinoethanol → HCID 178501203, compound

HRID 518610Notes

Reaction equation

HRID 518610 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:13]1[CH:18]=[C:17]([NH:19][C@@H:20]2[CH2:25][CH2:24][C@H:23]([C:26]([O:28][CH3:29])=[O:27])[CH2:22][CH2:21]2)[C:16]([N+:30]([O-:32])=[O:31])=[CH:15][N:14]=1>C1COCC1>[N+:30]([C:16]1[C:17]([NH:19][C@@H:20]2[CH2:21][CH2:22][C@H:23]([C:26]([O:28][CH3:29])=[O:27])[CH2:24][CH2:25]2)=[CH:18][C:13]([O:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:14][CH:15]=1)([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 18232N-PiperidinoethanolHCID 24758Sodium hydrideHCID 178501197HCID 178501197, compound

Product 1

HCID 178501203HCID 178501203, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a nitrogen purged, cooled (0° C.) suspension of 2-(piperidin-1-yl)ethanol (0.577 g, 4.46 mmol) in THF was added sodium hydride (0.196 g of 60% oil dispersion, 4.91 mmol), and the resulting mixture was stirred for 30 minutes. A solution of cis-methyl 4-(2-chloro-5-nitropyridin-4-ylamino)cyclohexanecarboxylate (1.40 g, 4.46 mmol) in THF (14 mL) was added, and the reaction was stirred overnight at RT. The reaction mixture was quenched with water (10 mL) and the product extracted with DCM (30 mL). The organic layer was collected, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10-30% of 90/10/1 DCM/MeOH/NH4OH in DCM) to afford cis-methyl 4-(5-nitro-2-(2-(piperidin-1-yl)ethoxy)pyridin-4-ylamino)cyclohexanecarboxylate (0.6 g, 33.1% yield). MS m/z=407.2 [M+H]. Calc'd for C20H30N4O5: 406.2.

Workup

  1. customTo a nitrogen purged
  2. temperaturecooled
  3. stirringthe reaction was stirred overnight at RT
  4. customThe reaction mixture was quenched with water (10 mL)
  5. extractionthe product extracted with DCM (30 mL)
  6. customThe organic layer was collected
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (10-30% of 90/10/1 DCM/MeOH/NH4OH in DCM)

Sources & evidence

ORD record
ord-da89f7ed3f92445cbc59359a4f7fc8e3
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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