1,2-Dibromoethane → HCID 14459743, compound

HRID 1904928Notes

Reaction equation

HRID 1904928 reaction equation
BrCCBr.[Mg].[CH3:6][N:7]1[CH2:12][CH2:11][CH:10](Cl)[CH2:9][CH2:8]1.[CH3:14][C:15]1[CH:31]=[CH:30][C:18]2[N:19]3[CH2:29][CH2:28][C:27]4[C:20]3=[C:21]([CH:24]=[CH:25][CH:26]=4)[CH:22]=[N:23][C:17]=2[CH:16]=1>O1CCCC1.C(OCC)(=O)C.[Cl-].[NH4+]>[CH3:14][C:15]1[CH:31]=[CH:30][C:18]2[N:19]3[CH2:29][CH2:28][C:27]4[C:20]3=[C:21]([CH:24]=[CH:25][CH:26]=4)[CH:22]([CH:10]3[CH2:11][CH2:12][N:7]([CH3:6])[CH2:8][CH2:9]3)[NH:23][C:17]=2[CH:16]=1

Participants

8

Reactant 4

HCID 78391,2-DibromoethaneHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 14459746HCID 14459746, compound

Product 1

HCID 14459743HCID 14459743, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

In a 1 L three-necked flask, 1,2-dibromoethane (0.3 ml) was added to a refluxing slurry of magnesium chips (4.1 gm) in tetrahydrofuran (80 ml) to initiate a Grignard reaction. A solution of N-methyl-4-chloropiperidine (28 ml) in tetrahydrofuran (30 ml) was added in portions to maintain a fast reflux. The resultant slurry was refluxed for 1 hour and cooled to about 0° C. A solution of 9-methyl-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (10.0 gm) in tetrahydrofuran (50 ml) was added dropwise. After 1.5 hours of stirring, the mixture was diluted with ethyl acetate (400 ml) and with saturated ammonium chloride solution (600 ml). The organic phase was separated. The aqueous phase was basified with 50% sodium hydroxide solution and then it was extracted twice with ethyl acetate (400 ml). The combined ethyl acetate solution was washed with water (2×300 ml) and brine (2×300 ml), dried over anhydrous magnesium sulfate, filtered and concentrated to a solid.

Workup

  1. customa Grignard reaction
  2. temperatureto maintain a fast reflux
  3. temperatureThe resultant slurry was refluxed for 1 hour
  4. customThe organic phase was separated
  5. extractionit was extracted twice with ethyl acetate (400 ml)
  6. washThe combined ethyl acetate solution was washed with water (2×300 ml) and brine (2×300 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-92ee6102ab1d4759a8e359c158834d32
Source dataset
uspto-grants-1989_06
Patent number
US04840947

Reaction notes

Loading…