Hydrogen Bromide → HCID 10198149, compound
Reaction equation
[CH3:1][N:2](C(OC(C)(C)C)=O)[CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH2:15])[CH:9]=1)[CH3:4].Br>>[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([NH2:15])[CH:9]=1)[CH3:4]Participants
3
Conditions
- Temperature
- 0 °C
Procedure
A solution of (4E)-N-methyl-N-(tert-butoxycarbonyl)-5-(3-amino-4-methylphenyl)-4-penten-2-amine (1.50 g, 4.93 mmol) and aqueous hydrobromic acid (50%, 25 mL) was stirred at 0° C. to ambient temperature for ˜16 h. The reaction mixture was extracted with chloroform (40 mL). The aqueous layer was cooled to 0° C. and basified with aqueous sodium hydroxide solution to pH 8-9 and extracted with chloroform (3×50 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated on a rotary evaporator to yield 0.938 g (93.3%) of a brown oil.
Workup
- extractionThe reaction mixture was extracted with chloroform (40 mL)
- extractionextracted with chloroform (3×50 mL)
- dry with materialThe combined extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated on a rotary evaporator
Sources & evidence
- ORD record
- ord-9b0afa5be8a24d09be88558af0d8cb39
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06337351B1
Reaction notes
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