Dimethyl Sulfoxide → [3-(5-Fluoro-1H-indol-3-yl)-propyl]-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl-methyl)-amine

HRID 427268Notes

Reaction equation

HRID 427268 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH:4](NC)[CH2:3]1.[F:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](C(Br)CC)=[CH:18]2.C([N:30]([CH2:33][CH3:34])[CH2:31]C)C.O.[CH3:36]S(C)=O>>[F:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:36][CH2:34][CH2:33][NH:30][CH2:31][CH:4]1[CH2:3][N:2]([CH3:1])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5]1

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8471TriethylamineHCID 540585145-Fluoro-indolyl-3-propylbromideHCID 699492554-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl-methylamine

Product 1

HCID 9841479[3-(5-Fluoro-1H-indol-3-yl)-propyl]-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl-methyl)-amineYield 47%

Procedure

A solution of 4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl-methylamine (0.45 g, 2.5 mmol) and 5-fluoro-indolyl-3-propylbromide (0.6 g, 2.5 mmol), and triethylamine (0.5 g) in dimethylsulfoxide (20 mL) was heated to 100° C. for 10 hours. The reaction mixture was poured into water (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and the solvent removed under vacuum. Chromatography (10% methanol-methylene chloride) afforded 0.42 g (47%) of desired product as a yellowish brown oil. The oxalate salt was prepared in ethanol: mp 189-190° C.

Workup

  1. extractionextracted with methylene chloride (3×50 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-7781fef0ae3c4465b00798c0eca31609
Source dataset
uspto-grants-2001_11
Patent number
US06313114B1

Reaction notes

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