Triethylamine → HCID 59700557, compound

HRID 901830Notes

Reaction equation

HRID 901830 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14]>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(OCC)(=O)C>[O:14]1[CH2:5][CH2:4][N:3]([C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][Br:8])[C:6]2[CH:7]=[CH:10][CH:11]=[CH:12][C:13]1=2

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 5211735-Bromovaleryl chloride

Product 1

HCID 59700557HCID 59700557, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,4-dihydro-2H-benzo[b]oxazine (500 mg, 1 eq, 3.7 mmol), triethylamine (1.54. ml, 3 eq, 11.1 mmol) and catalytic amount of DMAP in dry DCM (20 ml) was added 5-bromo pentanoyl chloride (870 μl, 2 eq, 7.40 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 4 h and then diluted with excess ethyl acetate. The ethyl acetate layer was washed with dil. HCl, water and then with brine. The residue was chromatographed with ethyl acetate and hexane to yield the title compound liquid (535 mg, yield 53%) as viscous liquid.

Workup

  1. washThe ethyl acetate layer was washed with dil. HCl, water
  2. customThe residue was chromatographed with ethyl acetate and hexane

Sources & evidence

ORD record
ord-c6a6eee0dcdc4418b716b9eddb9290bc
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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