1,2-Dibromoethane → HCID 14459741, compound

HRID 1904925Notes

Reaction equation

HRID 1904925 reaction equation
BrCCBr.[Mg].[CH3:6][N:7]1[CH2:12][CH2:11][CH:10](Cl)[CH2:9][CH2:8]1.[Br:14][C:15]1[CH:16]=[C:17]2[CH2:26][CH2:25][N:24]3[C:18]2=[C:19]([CH:32]=1)[CH:20]=[N:21][C:22]1[CH:30]=[C:29]([Br:31])[CH:28]=[CH:27][C:23]=13.[OH-].[NH4+]>O1CCCC1.ClCCl>[Br:14][C:15]1[CH:16]=[C:17]2[CH2:26][CH2:25][N:24]3[C:18]2=[C:19]([CH:32]=1)[CH:20]([CH:10]1[CH2:11][CH2:12][N:7]([CH3:6])[CH2:8][CH2:9]1)[NH:21][C:22]1[CH:30]=[C:29]([Br:31])[CH:28]=[CH:27][C:23]=13

Participants

8

Reactant 5

HCID 78391,2-DibromoethaneHCID 14923Ammonium HydroxideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 20036321HCID 20036321, compound

Product 1

HCID 14459741HCID 14459741, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

1,2-Dibromoethane (0.5 ml) was added to a refluxing slurry of magnesium chips (6 gm) in tetrahydrofuran (70 ml) to initiate a Grignard reaction. A solution of N-methyl-4-chloropiperidine (35 ml) in tetrahydrofuran (100 ml) was added rapidly. The reaction mixture was refluxed for 2 hours, during which a white precipitate formed. The mixture was cooled to room temperature and transferred to a flask containing 4,9-dibromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (20 gm) in tetrahydrofuran (200 ml) in one portion at ice-temperature. After 1 hour of stirring, the mixture was poured into ice-water/concentrated hydrochloric acid (600 ml:35 ml), and stirred for 15 minutes. The acid solution was slowly added to a stirred mixture prepared from dichloromethane (1 L) and an ammonium hydroxide solution (40 ml). The organic solution was separated, washed with water (500 ml) and brine (2×500 ml) and dried over anhydrous magnesium sulfate. The solution was filtered and concentrated to an oil (26 gm).

Workup

  1. customa Grignard reaction
  2. temperatureThe reaction mixture was refluxed for 2 hours, during which a white precipitate
  3. customformed
  4. customtransferred to a flask
  5. stirringstirred for 15 minutes
  6. additionThe acid solution was slowly added to a stirred mixture
  7. customThe organic solution was separated
  8. washwashed with water (500 ml) and brine (2×500 ml)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe solution was filtered
  11. concentrationconcentrated to an oil (26 gm)

Sources & evidence

ORD record
ord-6afa152b4e2141579de18830871c4bc0
Source dataset
uspto-grants-1989_06
Patent number
US04840947

Reaction notes

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