Methanol → HCID 131730301, compound

HRID 1946906Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:16])[N:13]=[C:12](OC)[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+:18].[CH3:19][OH:20]>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:16])[CH2:9][O:10][CH2:11][C:12]([NH2:18])=[N:13]2)[CH:5]=[CH:6][CH:7]=1.[NH2:18][C:8]1[NH:13][O:20][CH:19]=[CH:3][CH:4]=1

Participants

Reactant 3

HCID 887Methanol

HCID 25517Ammonium Chloride

HCID 58155280(RS)-3-(3-Bromo-phenyl)-5-methoxy-3-methyl-3,6-dihydro-2H[1,4]oxazine

Product 1

HCID 131730301HCID 131730301, compound

Conditions

Temperature: 100 °C

Procedure

A dried pressure tube was charged with a dispersion of (RS)-3-(3-bromo-phenyl)-5-methoxy-3-methyl-3,6-dihydro-2H[1,4]oxazine (3.91 g, 14 mmol) and ammonium chloride (4.42 g, 83 mmol) in methanol (140 ml). The tube was sealed and heated at 100° C. overnight. After cooling, the reaction mixture was evaporated to dryness. The crude product was purified on an Isolute flash NH2 column using a gradient of dichloromethane/methanol=100/0 to 75/25 as the eluent. The (RS)-5-(3-bromo-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine was obtained as a light yellow foam (2.71 g, 73% of theory). MS (ISP): m/z=269.2 [M+H]+, 271.1 [M+2+H]+.

Workup

customThe tube was sealed
temperatureAfter cooling
customthe reaction mixture was evaporated to dryness
customThe crude product was purified on an Isolute flash NH2 column

Sources & evidence

ORD record: ord-493c5e859d3040adb49fa34209cce7a7
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399459B2

Reaction notes

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