Sodium hydride → HCID 57937566, compound

HRID 910911Notes

Reaction equation

HRID 910911 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].[Cl:17][C:18]1[CH:23]=[C:22]([N+]([O-])=O)[CH:21]=[CH:20][N:19]=1>>[Cl:17][C:18]1[CH:23]=[C:22]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH:21]=[CH:20][N:19]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 57937566HCID 57937566, compoundYield 84%

Procedure

Using the method of Example 3, Step A, tert-butyl 4-hydroxypiperidine-1-carboxylate (1.90 g, 9.46 mmol), 60% sodium hydride in mineral oil (378 mg, 9.46 mmol), and 2-chloro-4-nitropyridine (1.50 g, 9.46 mmol) were reacted to provide tert-butyl 4-(2-chloropyridin-4-yloxy)piperidine-1-carboxylate (2.48 g, 84% yield) as an oil. 1H NMR (CDCl3) δ 8.19 (d, 1H), 6.83 (s, 1H), 6.74 (d, 1H), 4.56 (m, 1H), 3.68 (ddd, 2H), 3.37 (ddd, 2H), 1.94 (dddd, 2H), 1.77 (dddd, 2H), 1.47 (s, 9H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1309b776a5c4451f9affb66309c8a957
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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