1,2-Dibromoethane → HCID 14459742, compound

HRID 1904926Notes

Reaction equation

HRID 1904926 reaction equation
BrCCBr.[Mg].[CH3:6][N:7]1[CH2:12][CH2:11][CH:10](Cl)[CH2:9][CH2:8]1.[F: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>[F: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

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 20036328HCID 20036328, compound

Product 1

HCID 14459742HCID 14459742, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
5 °C

Procedure

In a dried 1 L three-necked flask, 1,2-dibromoethane (0.5 ml) was added to a refluxing slurry of magnesium chips (6.3 gm) in tetrahydrofuran (50 ml) to initiate a Grignard reaction. The mixture became cloudy and a vigorous reaction ensued. A solution of N-methyl-4-chloropiperidine (37 ml) in tetrahydrofuran (40 ml) was added in portions to maintain a fast reflux over a period of 10 minutes. The resultant slurry was refluxed for 1.5 hours and thereafter cooled to about 5° C. with an ice-water bath. A solution of 9-fluoro-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine (15.7 gm) in tetrahydrofuran (70 ml) was added in 5 minutes. The mixture was stirred for 40 minutes.

Workup

  1. customa Grignard reaction
  2. temperatureto maintain
  3. temperaturea fast reflux over a period of 10 minutes
  4. temperatureThe resultant slurry was refluxed for 1.5 hours

Sources & evidence

ORD record
ord-ef5a34f759fc434e87d63d8e582791ed
Source dataset
uspto-grants-1989_06
Patent number
US04840947

Reaction notes

Loading…