Hydrogen Bromide → Aminobenzodiazepine

HRID 1635113Notes

Reaction equation

HRID 1635113 reaction equation
Br.[NH2:2][C:3]1[CH:9]=[CH:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[NH:5][N:4]=1.Br>C(Cl)Cl.CCOCC>[NH2:2][C:3]1[CH:9]=[CH:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[NH:5][N:4]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 68936842racemic aminobenzodiazepine HBr salt

Product 1

HCID 21955614AminobenzodiazepineYield 230.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

The crude product 7 (1.0 g, 2.4 mmol) from the above reaction was dissolved in methylene chloride (10 mL), treated with anhydrous HBr gas for 1 h until disappearance of 7 on TLC. The reaction mixture was diluted with ether (100 mL) and decanted. The precipitates were washed with ether and decanted (3×100 mL). The remaining ether was removed in vacuo and the residue was dried under vacuum to afford 8 (0.88 g, 100%) as a white solid. MS m/z 366.0 (MH+), 286.1 (MH+−HBr).

Workup

  1. customdecanted
  2. washThe precipitates were washed with ether
  3. customdecanted (3×100 mL)
  4. customThe remaining ether was removed in vacuo
  5. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-eb01afb3a1524ad4b627988c3406dce4
Source dataset
uspto-grants-2003_01
Patent number
US06509333B2

Reaction notes

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