Benzene, 1-bromo-3-(trifluoromethyl)- → HCID 23039573, compound

HRID 1284201Notes

Reaction equation

HRID 1284201 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:7][CH:8]=1.[CH:13]1([C:16](=[O:25])[CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1.[Cl-:26].[NH4+]>CCOCC>[ClH:26].[CH:13]1([C:16]([C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:4]=2)([OH:25])[CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 21488082HCID 21488082, compound

Product 1

HCID 23039573HCID 23039573, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A stirred ether solution of a Grignard reagent prepared from 14.5 g. (0.6 mole) of magnesium, 136 g. (0.6 mole) of 3-bromo-benzotrifluoride and 800 ml. of dry ether treated at -20°C. to -30°C. with 53.5 g. (0.296 mole) of crude 1-cyclopropyl-3-piperidino-1-propanone in 200 ml. of ether. After addition the reaction mixture was stirred and allowed to warm to room temperature over 1 hour. The reaction mixture was treated with 32 g. of ammonium chloride in 170 ml. of water and the ether layer separated. The aqueous fraction was filtered and the solid precipitate was extracted with five 200 ml. portions of ether. The combined ether extracts were dried over magnesium sulfate and concentrated to an oil. Distillation under reduced pressure gave an oil which was converted to the hydrochloride salt. Recrystallization from acetone-ethanol mixture gave 3.6 g. (17%) of pure product which melted at 193°-194°C.

Workup

  1. additionAfter addition the reaction mixture
  2. additionThe reaction mixture was treated with 32 g
  3. customof water and the ether layer separated
  4. filtrationThe aqueous fraction was filtered
  5. extractionthe solid precipitate was extracted with five 200 ml
  6. dry with materialThe combined ether extracts were dried over magnesium sulfate
  7. concentrationconcentrated to an oil
  8. distillationDistillation under reduced pressure
  9. customgave an oil which
  10. customRecrystallization from acetone-ethanol mixture
  11. customgave 3.6 g

Sources & evidence

ORD record
ord-7f483dba52c8483ab345443a56f0e9b5
Source dataset
uspto-grants-1976_08
Patent number
US03978130

Reaction notes

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