Hydrochloric Acid → 1-Allyl-7-bromo-2,3-dihydro-1-benzazepine-4-carboxylic acid

HRID 586982Notes

Reaction equation

HRID 586982 reaction equation
[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Br:15])=[CH:14][C:9]=2[CH:8]=[C:7]([C:16]([O:18]CC=C)=[O:17])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].N1CCOCC1.O.Cl>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Br:15])=[CH:14][C:9]=2[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8083MorpholineHCID 22329223Allyl 1-allyl-7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate

Product 1

HCID 223292791-Allyl-7-bromo-2,3-dihydro-1-benzazepine-4-carboxylic acidYield 99.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl 1-allyl-7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (224 mg) in tetrahydrofuran (10 ml) were added tetrakistriphenylphosphinepalladium (74 mg) and morpholine (560 mg), and the mixture was stirred under argon atmosphere at room temperature for 2 hours. To the mixture was added water at 0° C., and the mixture was made acidic (pH=4) with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, further with water and saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give 1-allyl-7-bromo-2,3-dihydro-1-benzazepine-4-carboxylic acid (198 mg) as yellow amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid, further with water and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-228ad3cd8e0d4f48ac1dcb0387cd6386
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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