1,2-Difluorobenzene → HCID 45097170, compound

HRID 1821985Notes

Reaction equation

HRID 1821985 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1F>CN(C=O)C>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:8][CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 97061,2-DifluorobenzeneHCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-

Product 1

HCID 45097170HCID 45097170, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

Dissolve 1-methyl-piperidin-4-ol (4.61 g) in DMF (25 mL) and add slowly to a suspension of sodium hydride (95%) (1.11 g) in DMF (25 mL) at room temperature. Heat the mixture in an oil bath at 65° C. After 30 min., add 1,2-difluorobenzene (4.56 g) and stir at 65° C. After 2 hr., partition between water and ether, dry over anhydrous sodium sulfate, evaporate to give a yellow oil (5.88 g, 70% yield). Mass spectrum (electric spray) m/z=210 (M+1); 1H NMR (CDCl3): 7.05 (m, 3H), 6.92 (m, 1H), 4.29 (m, 1H), 2.71 (m, 2H), 2.30 (s, 3H), 2.27 (m, 2H), 1.99 (m, 2H), 1.89 (m, 2H).

Workup

  1. waitAfter 2 hr
  2. custom, partition between water and ether
  3. dry with materialdry over anhydrous sodium sulfate
  4. customevaporate

Sources & evidence

ORD record
ord-6a33e93c8d484e6c9ce311eb04cc24f3
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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