Tetrahydrofuran → Tert-butyl 4-(3-chloro-4-nitrobenzylidene)piperidine-1-carboxylate

HRID 515311Notes

Reaction equation

HRID 515311 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH2:5]P(=O)(OCC)OCC.O=[C:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.O1CCCC1.[H-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH:5]=[C:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 86654007Diethyl 3-chloro-4-nitrobenzylphosphonate

Product 1

HCID 67192823Tert-butyl 4-(3-chloro-4-nitrobenzylidene)piperidine-1-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethyl 3-chloro-4-nitrobenzylphosphonate (2.80 mmol, 0.86 g), tert-butyl 4-oxopiperidine-1-carboxylate (2.80 mmol, 0.557 g) and tetrahydrofuran (4.89 mL) were stirred and sodium hydride (4.19 mmol, 0.168 g) was added. The reaction was stirred overnight at room temperature. Water was added and the reaction extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated under vacuum to afford the intermediate tert-butyl 4-(3-chloro-4-nitrobenzylidene)-piperidine-1-carboxylate (0.85 g).

Workup

  1. extractionthe reaction extracted with dichloromethane
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ed03faf0f4fb4c888892eeb605cb7660
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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