Sodium hydride → HCID 57893591, compound

HRID 1821988Notes

Reaction equation

HRID 1821988 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][CH2:5]1.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14](F)[CH:13]=1>CN(C=O)C>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[C:16]([CH:17]=1)[O:3][CH:4]1[CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-HCID 1710404-Bromo-2-fluorotoluene

Product 1

HCID 57893591HCID 57893591, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (60% dispersion in oil, 880 mg, 22 mmol) to a solution of 4-hydroxy-1-methyl-piperidine (2.304 g, 20 mmol) in DMF (12 mL), stir. After 30 min., add 4-bromo-2-fluorotoluene (4.159 g, 22 mmol) and beat at 70° C. After 21 hr., quench the reaction with saturated NaHCO3 solution, extract with ether three times, combine the organic layers, wash with saturated NaCl solution, dry over Na2SO4, filter and concentrate to give a residue. Purify by chromatography (silica gel, eluting with 6% 2M NH3-methanol in CH2Cl2) provides of the title compound as a slightly yellow oil (3.90 g, 69%). Mass spectrum (ion spray): m/z=284.0 (M+1); 1H NMR (CDCl3, ppm): 7.01 (m, 3H), 4.35 (m, 1H), 2.66 (m, 2H), 2.36 (m, 2H), 2.34 (s, 3H), 2.19 (s, 3H), 2.03 (m, 2H), 1.85 (m, 2H).

Workup

  1. custombeat at 70° C
  2. waitAfter 21 hr
  3. custom, quench
  4. customthe reaction with saturated NaHCO3 solution
  5. extractionextract with ether three times
  6. washwash with saturated NaCl solution
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate
  10. customto give a residue
  11. customPurify by chromatography (silica gel, eluting with 6% 2M NH3-methanol in CH2Cl2)

Sources & evidence

ORD record
ord-40d7b1039bf244cc851997aa13aca7e1
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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