Sodium hydride → HCID 44339070, compound

HRID 1264533Notes

Reaction equation

HRID 1264533 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([NH:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[C:26]1([CH2:25][N:12]([C:10]2[O:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=2)[CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1378441-(Bromomethyl)naphthaleneHCID 13261901HCID 13261901, compound

Product 1

HCID 44339070HCID 44339070, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-phenyl-isoxazol-5-yl-(3-piperidin-1-yl-propyl)amine (142.5 mg, 0.0005 m) in DMF (6 ml) was added 25 mg 60% sodium hydride in oil. The reaction foamed and turned yellow. After stirring for 5 minutes, 110.5 mg 1-(bromomethyl)naphthalene in DMF (3 ml) was added. The reaction turned from yellow to brown in color. The DMF was removed under reduced pressure. The oil was flash chromatographed using a 50 mm×6″ silica gel column with methylene chloride 95-methanol 5-ammonium hydroxide 0.5 as the solvent system. The product fractions were collected and concentrated to an oil. Add hexane/ether and remove under reduced pressure (2×s). Ethanol was added followed by 1M HCl in ether (1 ml). Remove the solvent. Add hexane/ether (2×s) to yield “title” as a foam. Dry under high vac. HPLC 95.43% at 215. Mass Spectra cal'd. 425.57; found 426.4. H NMR (CDCl3) 11.95-11.75(br,s,1H), 8.1-7.3(m, 12H), 5.6-5.4(s,1H), 5.2-4.8(s,2H), 3.6-3.4(br,2H)3.35-3.15(br,2H), 2.7-2.5(br, 2H),2.3-2.0(br,6H.)

Workup

  1. customThe DMF was removed under reduced pressure
  2. customchromatographed
  3. customThe product fractions were collected
  4. concentrationconcentrated to an oil
  5. customAdd hexane/ether and remove under reduced pressure (2×s)
  6. additionEthanol was added
  7. customRemove the solvent
  8. customAdd hexane/ether (2×s) to yield “title” as a foam
  9. customDry under high vac

Sources & evidence

ORD record
ord-5ee068e728234955b4880b026bc67187
Source dataset
uspto-grants-2003_04
Patent number
US06544982B1

Reaction notes

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