Stannous Chloride → 2-Cyclopropyl-7-fluoro-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

HRID 131334Notes

Reaction equation

HRID 131334 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([NH:12][C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=3[N+:20]([O-])=O)=[C:8]([CH:11]=2)[C:9]#[N:10])[CH2:3][CH2:2]1.[Sn](Cl)[Cl:24]>C(O)C.Cl>[ClH:24].[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]3[NH:12][C:13]4[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=4[N:20]=[C:9]([NH2:10])[C:8]=3[CH:11]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 586258745-Cyclopropyl-2-(5-fluoro-2-nitro-phenylamino)-benzonitrile

Product 1

HCID 692138672-Cyclopropyl-7-fluoro-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideYield 61%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent

Procedure

Heat a solution of 5-cyclopropyl-2-(5-fluoro-2-nitro-phenylamino)-benzonitrile (0.447 g, 1.50 mmol) in ethanol (7 ml) to 60° C. Add a solution of tin (II) chloride (0.855 g, 4.51 mmol) in 5.0 N hydrochloric acid (7 ml) and heat the resulting mixture to reflux for 16 hours. Cool the reaction to room temperature, add 25 ml of 5.0 N hydrochloric acid and place the mixture in a freezer for 16 hours. Collect by filtration the precipitated product from the solution. Wash solid with 5.0 N hydrochloric acid to obtain 0.277 g of the title compound (0.91 mmol, 61% yield) as a yellow amorphous solid: Mass Spectrum (m/e): 268(M+1).

Workup

  1. temperatureheat the resulting mixture
  2. temperatureto reflux for 16 hours
  3. temperatureCool
  4. customthe reaction to room temperature
  5. filtrationCollect by filtration the precipitated product from the solution
  6. washWash solid with 5.0 N hydrochloric acid

Sources & evidence

ORD record
ord-4dde9add43aa4955b7a0a0f32d98d308
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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