Dibromomethane → HCID 57839202, compound

HRID 425283Notes

Reaction equation

HRID 425283 reaction equation
[Mg].C(Br)Br.Cl[CH:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1.[Br:13][C:14]1[CH:15]=[CH:16][C:17]2[C:23](=[O:24])[C:22]3[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=3[CH2:20][O:19][C:18]=2[CH:29]=1>C1COCC1>[Br:13][C:14]1[CH:15]=[CH:16][C:17]2[C:23]([CH:6]3[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]3)([OH:24])[C:22]3[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=3[CH2:20][O:19][C:18]=2[CH:29]=1

Participants

6

Reactant 4

HCID 3024DibromomethaneHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 22998939HCID 22998939, compound

Product 1

HCID 57839202HCID 57839202, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium turnings (3.42 g, 143 mmol) were suspended in 15 mL of dry THF under nitrogen. To this was added CH2Br2 (1.25 mL, 14.5 mmol) and a vigorous reaction was observed. The reaction was heated to reflux, and 4-chloro-1-methyl-piperidine (21 mL, 128 mmol) was added. The reaction was refluxed for 1 h. The reaction was allowed to cool, and the supernatant was transferred via cannula to a stirring solution of compound 2c (8 g, 128 mmol) in THF at room temperature. The slurry was rinsed with 2×20 mL THF and the supernatant was transferred. At that time, all of the starting ketone had been consumed. To the reaction was added saturated sodium bicarbonate, and the mixture was extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated. The crude product Compound 1d was used without further purification. MS m/z (MH+) 388.14.

Workup

  1. customa vigorous reaction
  2. temperatureThe reaction was heated
  3. temperatureto reflux
  4. temperatureThe reaction was refluxed for 1 h
  5. temperatureto cool
  6. washThe slurry was rinsed with 2×20 mL THF
  7. customAt that time, all of the starting ketone had been consumed
  8. additionTo the reaction was added saturated sodium bicarbonate
  9. extractionthe mixture was extracted with ethyl acetate
  10. dry with materialThe combined organics were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude product Compound 1d was used without further purification

Sources & evidence

ORD record
ord-c8ec5ad94ad14c3d84762b6a9d44e1d7
Source dataset
uspto-grants-2012_01
Patent number
US08106207B2

Reaction notes

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