Sodium hydride → HCID 57933849, compound

HRID 713181Notes

Reaction equation

HRID 713181 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[OH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.[H-].[Na+]>C1COCC1>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([O:11][CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]2)=[C:2]([F:1])[CH:3]=1)#[N:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5872033,4-DifluorobenzonitrileHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 57933849HCID 57933849, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3,4-difluorobenzonitrile (28 g, 201 mmol) and tert-butyl 4-hydroxypiperidine-1-carboxylate (40.5 g, 201 mmol) in THF (500 mL) was treated with sodium hydride (4 g, 100 mmoL) and stirred at 25° C. for 16 h. The reaction mixture was washed with water, extracted with EtOAc, and the crude product purified by flash silica gel chromatography gave tert-butyl 4-(4-cyano-2-fluorophenoxy)piperidine-1-carboxylate (25 g, 39%).

Workup

  1. washThe reaction mixture was washed with water
  2. extractionextracted with EtOAc
  3. customthe crude product purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-ea65a09643e84d069d1ddb4b9e185912
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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