Methanol → HCID 15225467, compound

HRID 2259566Notes

Reaction equation

HRID 2259566 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]3[CH2:18][CH:19]([CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][N:26]([C:29]5[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][N:30]=5)[CH2:25][CH2:24]4)[O:20][C:15]4[C:16]3=[C:11]([CH:12]=[CH:13][CH:14]=4)[C:10]=2[CH3:36])=[CH:5][CH:4]=1.B(Br)(Br)Br.CO>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:17]3[CH2:18][CH:19]([CH2:21][CH2:22][N:23]4[CH2:24][CH2:25][N:26]([C:29]5[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][N:30]=5)[CH2:27][CH2:28]4)[O:20][C:15]4[C:16]3=[C:11]([CH:12]=[CH:13][CH:14]=4)[C:10]=2[CH3:36])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 15225466HCID 15225466, compound

Product 1

HCID 15225467HCID 15225467, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.9 g of 2,3-dihydro-5-(4-methoxyphenyl)-6-methyl-2-[2-(4-(4-methylpyridin-2-yl)piperazin-1-yl)ethyl]pyrrolo[1,2,3-de]-1,4-benzoxazine (Preparation see Example 1) were dissolved in 5 ml of anhydrous dichloromethane under a nitrogen atmosphere. The solution was cooled to 0° to 5° C. and 1.5 g of boron tribromide were then added all at once. The reaction mixture was subsequently stirred for 3 hours at room temperature. The reaction mixture was then again cooled to 0° to 5° C. and 10 ml of methanol were added, and the reaction mixture was again stirred for half an hour at room temperature and then evaporated. The residue was dissolved in 20 ml of aqueous ammonia solution (pH=8/9) and the solution was extracted with dichloromethane. The extracts were dried, filtered and concentrated. The crude title compound remaining as a residue was purified by column chromatography using toluene/ethanol 95:5 and crystallized from isopropanol. 1.5 g of 2,3-dihydro-5-(4-hydroxyphenyl)-6-methyl-2-[2-(4-(4-methylpyridin-2-yl)piperazin-1-yl)ethyl]pyrrolo[1,2,3-de]-1,4-benzoxazine were obtained as a white powder having a melting point of 213° to 214° C.

Workup

  1. temperatureThe solution was cooled to 0° to 5° C.
  2. temperatureThe reaction mixture was then again cooled to 0° to 5° C.
  3. stirringthe reaction mixture was again stirred for half an hour at room temperature
  4. customevaporated
  5. dissolutionThe residue was dissolved in 20 ml of aqueous ammonia solution (pH=8/9)
  6. extractionthe solution was extracted with dichloromethane
  7. customThe extracts were dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customwas purified by column chromatography
  11. customcrystallized from isopropanol

Sources & evidence

ORD record
ord-3b1d1aca223042a9be7830fc08e18c24
Source dataset
uspto-grants-1995_12
Patent number
US05474988

Reaction notes

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