7-Benzenesulfonyl-4-(1-benzyl-pyrrolidin-3-yl)-3,4-dihydro-2H-benzo[1,4]oxazine → 7-benzenesulfonyl-4-pyrrolidin-3-yl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 2224082Notes

Reaction equation

HRID 2224082 reaction equation
[C:1]1([S:7]([C:10]2[CH:31]=[CH:30][C:13]3[N:14]([CH:18]4[CH2:22][CH2:21][N:20](CC5C=CC=CC=5)[CH2:19]4)[CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd].C(O)(=O)C>[C:1]1([S:7]([C:10]2[CH:31]=[CH:30][C:13]3[N:14]([CH:18]4[CH2:22][CH2:21][NH:20][CH2:19]4)[CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 586415207-Benzenesulfonyl-4-(1-benzyl-pyrrolidin-3-yl)-3,4-dihydro-2H-benzo[1,4]oxazine

Product 1

HCID 116098757-benzenesulfonyl-4-pyrrolidin-3-yl-3,4-dihydro-2H-benzo[1,4]oxazineYield 44.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-Benzenesulfonyl-4-(1-benzyl-pyrrolidin-3-yl)-3,4-dihydro-2H-benzo[1,4]oxazine (0.127 g, 0.292 mmol) was dissolved in 15 mL ethanol and this solution was added to a flask containing 35 mg of 5% palladium on charcoal, followed by 3 drops of glacial acetic acid. The system was purged with hydrogen gas and stirring was continued for 24 hours under 1 atm. of hydrogen gas. The reaction mixture was filtered through celite, the filtrate concentrated in vacuo, and the resulting solid purified by flash (6:0.4:0.04 of CH2Cl2:MeOH:NH4OH) to give 45 mg of 7-benzenesulfonyl-4-pyrrolidin-3-yl-3,4-dihydro-2H-benzo[1,4]oxazine as free base. This solid was dissolved in 1 mL methanol and combined with 0.5 mL of 2N ethanolic hydrogen chloride and the resulting solution is concentrated in vacuo and subjected to a vacuum of 0.3 Torr for 2 hours to give a foam which was triturated twice with 50 mL ethyl ether to give, after drying under reduced pressure, 25 mg (0.07 mmol, 25%) of 7-benzenesulfonyl-4-pyrrolidin-3-yl-3,4-dihydro-2H-benzo[1,4]oxazine hydrochloride as a tan solid. MS: 345 (M+H)+, mp: 122.8-127.6° C.

Workup

  1. additionthis solution was added to a flask
  2. customThe system was purged with hydrogen gas
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate concentrated in vacuo
  5. customthe resulting solid purified by flash (6:0.4:0.04 of CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-64ac33af5d1642c990f0b6f3b2f15b4a
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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