Dimethyl Sulfoxide → HCID 67517884, compound

HRID 514877Notes

Reaction equation

HRID 514877 reaction equation
CS(C)=O.F[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].[OH:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>O>[OH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[C:9]#[N:10])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 678803-FluorobenzonitrileHCID 79341Piperidin-4-ol

Product 1

HCID 67517884HCID 67517884, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dimethylsulfoxide (30 mL) solution of 3-fluorobenzonitrile (9.73 g, 80.0 mmol) and 4-hydroxypiperidine (8.15 g, 81 mmol) was heated to 100° C. and stirred for 5 hours. The solution was cooled to room temperature and added dropwise to water (500 mL). The mixture was extracted with ethyl acetate (2×300 mL) and washed with water (2×200 mL), brine (200 mL), dried (magnesium sulfate) and concentrated in vacuo to afford the crude product. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×300 mL)
  2. washwashed with water (2×200 mL), brine (200 mL)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product
  6. washChromatography over silica gel, eluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-b3f21a86062f46b4b98ada1d190c82f8
Source dataset
uspto-grants-2015_08
Patent number
US09108920B2

Reaction notes

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