Hydrochloric Acid → HCID 15225472, compound

HRID 2259571Notes

Reaction equation

HRID 2259571 reaction equation
[CH3:1][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][C:23]([N:25]4[CH2:30][CH2:29][N:28]([C:31]5[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][N:32]=5)[CH2:27][CH2:26]4)=O)[O:20][C:15]4[C:16]3=[C:11]([CH:12]=[CH:13][CH:14]=4)[C:10]=2[CH3:38])=[CH:5][CH:4]=1.Cl>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:17]3[CH2:18][CH:19]([CH2:21][CH2:22][CH2:23][N:25]4[CH2:26][CH2:27][N:28]([C:31]5[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][N:32]=5)[CH2:29][CH2:30]4)[O:20][C:15]4[C:16]3=[C:11]([CH:12]=[CH:13][CH:14]=4)[C:10]=2[CH3:38])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15225471HCID 15225471, compound

Product 1

HCID 15225472HCID 15225472, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 g of 2,3-dihydro-5-(4-methoxyphenyl)-6-methyl-2-[3-(4-(4-methylpyridin-1-yl)piperazin-1-yl) -3-oxopropyl]pyrrolo[1,2,3-de]-1,4-benzoxazine (prepared according to Example 6)) was dissolved in 15 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere. 12 ml of a 1 molar borane-tetrahydrofuran complex were added to the solution. The reaction mixture was stirred and heated to reflux for 2 hours. 25 ml of a 6N hydrochloric acid solution were then added and the reaction mixture was stirred for 24 hours. The precipitate formed was dissolved in water which was rendered alkaline (pH=12), and the solution was extracted with dichloromethane. The organic extracts were dried and evaporated. The crude product remaining was purified by column chromatography using dichloromethane containing 2% ethanol as an eluent. The purified title compound was poured into 3N isopropanolic hydrochloric acid solution for conversion into its dihydrochloride salt. 0.6 g of 2,3-dihydro-5-(4-methoxyphenyl)-6-methyl-2-[3-(4-(4-methylpyridin-2-yl)piperazin-1-yl)propyl]pyrrolo[1,2,3-de]-1,4-benzoxazine. 2HCl.0.7H2O was obtained as yellow crystals having a melting point of 248° to 249° C.

Workup

  1. addition12 ml of a 1 molar borane-tetrahydrofuran complex were added to the solution
  2. temperatureheated
  3. temperatureto reflux for 2 hours
  4. stirringthe reaction mixture was stirred for 24 hours
  5. customThe precipitate formed
  6. extractionthe solution was extracted with dichloromethane
  7. customThe organic extracts were dried
  8. customevaporated
  9. customThe crude product remaining was purified by column chromatography
  10. customThe purified title compound
  11. additionwas poured into 3N isopropanolic hydrochloric acid solution for conversion into its dihydrochloride salt
  12. custom0.7H2O was obtained as yellow crystals

Sources & evidence

ORD record
ord-53b4bd5be9cd4b469f94397e45e12fcb
Source dataset
uspto-grants-1995_12
Patent number
US05474988

Reaction notes

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