Sodium hydride → HCID 66745671, compound

HRID 1467192Notes

Reaction equation

HRID 1467192 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[N+:19]([C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([N+]([O-])=O)[C:23]=1[C:24]#[N:25])([O-:21])=[O:20]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:26]2[CH:27]=[CH:28][CH:29]=[C:22]([N+:19]([O-:21])=[O:20])[C:23]=2[C:24]#[N:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 520718DinitrobenzonitrileHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 66745671HCID 66745671, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of tert-butyl-4-(2-hydroxyethyl)piperidine-1-carboxylate (769 μL, 3.50 mmol) and NaH (118 mg, 3.50 mmol, 60% dispersion in mineral oil) in dry DMF (5 mL) at 0° C., was added a solution of 2,6-dinitrobenzonitrile (614 mg, 3.18 mmol) in dry DMF (4 mL). The reaction was stirred under N2, warming to rt. Upon completion, the reaction was quenched with H2O (50 mL), and the precipitate was collected by vacuum filtration to provide tert-butyl-4-(2-(2-cyano-3-nitrophenoxy)ethyl)piperidine-1-carboxylate (955 mg, 80%) as a tan solid 1H NMR (400 MHz, CDCl3) δ 1.09 (m, 2H), 1.40 (s, 9H), 1.73 (m, 5H), 2.70 (m, 2H), 3.94 (m, 2H), 4.32 (t, J=6.8 Hz, 2H), 7.75 (m, 1H), 7.92 (m, 2H).

Workup

  1. customUpon completion, the reaction was quenched with H2O (50 mL)
  2. filtrationthe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-8cd110229a7d4b1b8a1da522095c6bf6
Source dataset
uspto-grants-2015_04
Patent number
US09000054B2

Reaction notes

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