Dichloromethane → HCID 11110612, compound

HRID 1603838Notes

Reaction equation

HRID 1603838 reaction equation
N1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH2:17][CH:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][N:14]=3)=[CH:9][CH:8]=2)CC=CCC1.C([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C.[C:30](Cl)(=[O:32])[CH3:31].[CH2:34](Cl)Cl>>[C:30]([N:25]1[CH2:26][CH:27]=[C:34]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH2:17][CH:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][N:14]=3)=[CH:11][CH:12]=2)[CH2:29][CH2:28]1)(=[O:32])[CH3:31]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 70111126HCID 70111126, compound

Product 1

HCID 11110612HCID 11110612, compound

Procedure

To a flask containing N-[[4,5-dihydro-3-[4-[1,2,3,6-tetrahydropyridinyl]-phenyl]-5-isoxazolyl]methyl]acetamide (300 mg, 1.00 mmol) in methylene chloride (15 mL) and triethylamine (0.28 mL, 2.00 mmol) is added acetyl chloride (0.08 mL, 1.10 mmol) at 0° C. under an inert atmosphere. The reaction is warmed to ambient temperature stirred fifteen hours, concentrated in vacuo, and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (98/2). The appropriate fractions are combined (Rf =0.18, TLC, chloroform/methanol, 95/5) and concentrated in vacuo to give the title compound, HRMS calcd for C19H23N3O3 : 341.1739. Found: 341.7125.

Workup

  1. concentrationconcentrated in vacuo
  2. customchromatographed on silica gel (230-400 mesh, 100 mL)
  3. washeluting with chloroform/methanol (98/2)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00501556aa594093a56bbcdd96ab0f02
Source dataset
uspto-grants-1999_11
Patent number
US05990136

Reaction notes

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