Diethyl Ether → HCID 58584388, compound
Reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.C(N(CC)CC)C.[Br:19][CH2:20][C:21](Br)=[O:22].CCOCC>C(Cl)Cl>[Br:19][CH2:20][C:21]([N:1]1[C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:22]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 0° C. solution of 2,3,4,5-Tetrahydro-1H-benzo[b]azepine (5.5 g, 37.4 mmol) and triethylamine (5.21 mL, 37.4 mmol) in anhydrous methylene chloride (180 mL) under N2 was added dropwise bromoacetyl bromide (3.25 mL, 37.4 mmol). The mixture was stirred at 0° C. for 2 h, then allowed to warm to ambient temperature and stirred for 1 h. The mixture was worked up by washing with 0.5 M aq. HCl (100 mL) and brine (100 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated to give the crude product as a brown semi-solid. Trituration with ether gave the product (5.69 g) as a tan solid.
Workup
- temperatureto warm to ambient temperature
- stirringstirred for 1 h
- washby washing with 0.5 M aq. HCl (100 mL) and brine (100 mL)
- customThe organic layer was separated
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto give the crude product as a brown semi-solid
Sources & evidence
- ORD record
- ord-4c01fff0aadb4022849e7e3f8b14ce77
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169773B2
Reaction notes
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