Triethylamine → HCID 19087731, compound

HRID 1464284Notes

Reaction equation

HRID 1464284 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[NH:12][C:11]1=[O:21])(=O)=O.[C:22]1([C:28]2[CH2:29][CH2:30][NH:31][CH2:32][CH:33]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C(OCC)(=O)C.O>[C:22]1([C:28]2[CH2:33][CH2:32][N:31]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13](=[O:20])[NH:12][C:11]3=[O:21])[CH2:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 19087664HCID 19087664, compound

Product 1

HCID 19087731HCID 19087731, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

A mixture of 1-(4-methanesulfonyloxybutyl)-2,4(1H,3H)-quinazolinedione (312 mg), 4-phenyl-1,2,3,6-tetrahydropyridine (200 mg) and triethylamine (303 mg) was refluxed for 1.5 hours. The reaction mixture was poured into ethyl acetate-water, extracted with ethyl acetate. Combined organic extract was washed in turn with water and brine, dried over magnesium sulfate, and evaporated. The crude residue was washed with hot methanol to give 1-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-2,4(1H,3H)-quinazolinedione (114 mg) as a powder.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. extractionCombined organic extract
  4. washwas washed in turn with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. washThe crude residue was washed with hot methanol

Sources & evidence

ORD record
ord-fe4b7ec930e3410184ad0e1e293c9428
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

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