Water → 7-Bromo-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid methyl ester

HRID 467559Notes

Reaction equation

HRID 467559 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Br:6][C:7]1[CH:17]=[CH:16][C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:9]=2[CH:8]=1.C(N(CC)CC)C.O>ClCCl>[CH3:5][O:4][C:2]([N:13]1[CH2:14][CH2:15][C:9]2[CH:8]=[C:7]([Br:6])[CH:17]=[CH:16][C:10]=2[CH2:11][CH2:12]1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 468400337-Bromo-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 674693277-Bromo-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid methyl esterYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl chloroformate (444 mg, 4.70 mmol) was added to a 0° C. mixture of 7-bromo-2,3,4,5-tetrahydro-1H-benzo[d]azepine (950 mg, 3.82 mmol) and triethylamine (915 mg, 9.04 mmol) in 19 mL of dichloromethane. The resulting solution was stirred at 0° C. for 2 h. Water was added, the layers were separated and the aqueous phase was washed with dichloromethane, and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to leave 1.07 g of an oil. This material was combined with 52 mg from an earlier experiment and purified by column chromatography on silica gel (24 g SiO2, Analogix column) eluting @ 30 mL/min with 1:1 ethyl acetate/heptane. 763 mg of product was obtained.

Workup

  1. customthe layers were separated
  2. washthe aqueous phase was washed with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-76f6df8389c44d94b299783fa7ce58e8
Source dataset
uspto-grants-2014_01
Patent number
US08623877B2

Reaction notes

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