3,4-Dihydro-2H-1,4-benzoxazine → HCID 86692007, compound

HRID 1505736Notes

Reaction equation

HRID 1505736 reaction equation
C(O[C:4]1([C:15]([F:18])([F:17])[F:16])[CH:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:5]1)C.[O:19]1[CH2:24][CH2:23][NH:22][C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]1=2>FC(F)(F)C(O)C(F)(F)F>[CH2:7]([CH:6]1[C:4]([C:15]([F:16])([F:17])[F:18])([OH:5])[C:25]2[C:21]3=[C:20]([O:19][CH2:24][CH2:23][N:22]13)[CH:28]=[CH:27][CH:26]=2)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 15651912HCID 15651912, compound

Product 1

HCID 86692007HCID 86692007, compound

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

A solution of 2-ethoxy-3-phenethyl-2-(trifluoromethyl)oxirane (340 mg, 1.3 mmol) and 3,4-dihydro-2H-benzo[b][1,4]oxazine (177 mg, 1.3 mmol) in hexafluoroisopropanol was stirred at room temperature overnight. The solvent was evaporated and the residue purified by reverse-phase HPLC (CH3CN/0.1% trifluoroacetic acid) to yield 5-phenethyl-6-(trifluoromethyl)-2,3,5,6-tetrahydro-[1,4]oxazino[2,3,4-hi]indol-6-ol as a solid (MS m/z 350 MH+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by reverse-phase HPLC (CH3CN/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-3bbf3a1c86294e18bc2848fbbd7f9440
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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