Hydrochloric Acid → HCID 20031347, compound

HRID 232303Notes

Reaction equation

HRID 232303 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[Mg].[CH2:10]([N:14]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]([C:21]#N)[CH2:15]1)[CH2:11][CH2:12][CH3:13].Cl.CC[O:26]CC>>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:21]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][N:14]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:15]2)=[O:26])=[CH:3][CH:4]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 99931-Bromo-4-fluorobenzeneHCID 5462224Magnesium2×HCID 20031349HCID 20031349, compound

Product 1

HCID 20031347HCID 20031347, compound

Procedure

To 25 mL of dry ether under N2 add 2 g (11 mmol) of 1-bromo-4-fluorobenzene and 0.25 g (0.10 mmol) of magnesium turnings. Initiate the reaction by standard procedures. When the magnesium filings are gone add 1 g (8.0 mmol) of 1-butyl-hexahydro-1H-azepine-3-carbonitrile and reflux the reaction mixture. Monitor the reaction by thin-layer chromatography. Upon completion add 50 mL 1M HCl and stir for one hr. The layers are separated and the aqueous layer is extracted with methylene chloride (25 mL). Add 4N NaOH to the aqueous layer until basic and extract with methylene chloride. Dry the organic phase over Na2SO4. Filter off the drying agent and evaporate the solvent in vacuo to obtain the title compound.

Workup

  1. customInitiate the reaction by standard procedures
  2. temperaturereflux the reaction mixture
  3. customMonitor the reaction by thin-layer chromatography
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with methylene chloride (25 mL)
  6. additionAdd 4N NaOH to the aqueous layer until basic and
  7. extractionextract with methylene chloride
  8. dry with materialDry the organic phase over Na2SO4
  9. filtrationFilter off the drying agent
  10. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-ed65bd1748e74875b5be36b0d3ec3e25
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Reaction notes

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