Methane → HCID 19087701, compound

HRID 1464291Notes

Reaction equation

HRID 1464291 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:19]=3[C:20]([NH2:22])=[O:21])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:28][C:29](OC(Cl)(Cl)Cl)=[O:30].C>O1CCOCC1>[ClH:28].[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[C:18]4[C:19](=[C:23]([F:27])[CH:24]=[CH:25][CH:26]=4)[C:20](=[O:21])[NH:22][C:29]3=[O:30])[CH2:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 10426DiphosgeneHCID 19087729HCID 19087729, compound

Product 1

HCID 19087701HCID 19087701, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[N-{4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butylamino-6-fluorobenzamide (900 mg), trichloromethyl chloroformate (1.5 ml) and active charcoal (catalytic amounts) in dioxane (20 ml) was stirred for 1 hour at 80° C. The solvent was removed in vacuo. The residue was dissolved in 10% hydrogen chloride-methanol, then the solution was filtered. After evaporation of the filtrate, the residue was crystallized from ethanol-ether. The crude crystals were collected, and washed with hot ethanol to afford 1-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-5-fluoro-2,4(1H,3H)-quinazolinedione hydrochloride (80 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in 10% hydrogen chloride-methanol
  3. filtrationthe solution was filtered
  4. customAfter evaporation of the filtrate
  5. customthe residue was crystallized from ethanol-ether
  6. customThe crude crystals were collected
  7. washwashed with hot ethanol

Sources & evidence

ORD record
ord-db4d985e646d48e381d0eed5090224f7
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

Loading…