Water → 3-Azido-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

HRID 1591437Notes

Reaction equation

HRID 1591437 reaction equation
I[CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:14].[N-:15]=[N+:16]=[N-:17].CN(C)C(=[NH2+])N(C)C.O>C(Cl)Cl>[N:15]([CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:14])=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 962WaterHCID 541990513-iodo-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-oneHCID 178484365HCID 178484365, compound

Product 1

HCID 538629013-Azido-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-oneYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

101 mg (0.33 mmol) of 3-iodo-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Step B) dissolved in 8.3 mL of methylene chloride and 105 mg (0.66 mmol, 2 eq) of tetramethylguanidinium azide was added. The mixture was stirred at room temperature for 16 hours then water was added and the layers allowed to separate. The organic layer was removed, washed with water and brine, then dried over magnesium sulfate, filtered and solvents removed under vacuum to afford 66 mg (0.30 mmol, 90%) of the product. 1H NMR (200 MHz, CDCl3): 2.28 (m,1H), 2.45 (m,1H), 2.73 (m,1H), 2.93 (m,1H), 3.86 (dd;8,11 Hz;1H), 7.0 (m,3H), 8.15 (br s,1H). FAB-MS: calculated for C10H9FN4O 220; found 221 (M+H,100%).

Workup

  1. customto separate
  2. customThe organic layer was removed
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvents removed under vacuum

Sources & evidence

ORD record
ord-ad12d909ed054f99986305ed99f2c3ca
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

Loading…