1,3-Dibromopropane → 2H-1,4-Benzoxazine, 4-(3-bromopropyl)-3,4-dihydro-

HRID 901827Notes

Reaction equation

HRID 901827 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2.[Br:11][CH2:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][N:4]([CH2:14][CH2:13][CH2:12][Br:11])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 10340Sodium CarbonateHCID 5850963,4-Dihydro-2H-1,4-benzoxazine

Product 1

HCID 114708452H-1,4-Benzoxazine, 4-(3-bromopropyl)-3,4-dihydro-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3,4-dihydro-2H-benzo[b][1,4]oxazine (3.0 g, 1 eq, 22.2 mmol), 1,3-dibromopropane (22.5 ml, 10 eq, 222 mmol) and anhydrous sodium carbonate (7.05 g, 3 eq, 66.6 mmol) in dry DMF (200 ml) was heated at 70° C. for 16 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The residue was chromatographed using ethyl acetate and hexane to yield the title compounds as liquid mass (2.6 g, 47%).

Workup

  1. washwashed with water and brine
  2. customThe residue was chromatographed

Sources & evidence

ORD record
ord-538ea71e18814810a68e0e9c5a8608eb
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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