Diisopropylamine → HCID 59799081, compound

HRID 1013106Notes

Reaction equation

HRID 1013106 reaction equation
[OH:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[I:26]N1C(=O)CCC1=O>C(Cl)Cl>[OH:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:15])[F:16])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[I:26]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 120273N-IodosuccinimideHCID 22219609HCID 22219609, compound

Product 1

HCID 59799081HCID 59799081, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
15 °C

Procedure

Add 6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.037 g, 4.0 mmol) and diisopropylamine (60.7 mg, 0.6 mmol) to anhydrous DCM (350 mL) and stir at 10-20° C. Add slowly a solution of N-iodosuccinimide (1.035 g, 4.6 mmol) in DCM (100 mL) over a period of 3 h. Stir the reaction mixture overnight and gradually warm to RT. Quench the reaction with saturated aqueous sodium bicarbonate, separate the organic layer, wash the organic layer with 0.1 N HCl, brine, dry (sodium sulfate) concentrate and purify (silica gel chromatography, eluting with 5:95 to 10:90 EtOAc:hexanes) to give the title compound as a white solid (1.0 g, 65%).

Workup

  1. stirringStir the reaction mixture overnight
  2. temperaturegradually warm to RT
  3. customQuench
  4. customthe reaction with saturated aqueous sodium bicarbonate
  5. customseparate the organic layer
  6. washwash the organic layer with 0.1 N HCl, brine
  7. dry with materialdry (sodium sulfate)
  8. concentrationconcentrate
  9. custompurify
  10. wash(silica gel chromatography, eluting with 5:95 to 10:90 EtOAc:hexanes)

Sources & evidence

ORD record
ord-5b0aeb0695894cbba1616769c4fc2c4e
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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