Ammonium Chloride → HCID 14770831, compound

HRID 1090370Notes

Reaction equation

HRID 1090370 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([Br:9])=[CH:4][C:3]=1[F:10].C([Li])CCC.[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1.[Cl-].[NH4+]>C(OCC)C.O>[Br:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([C:20]2([OH:23])[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]2)=[C:3]([F:10])[CH:4]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 675961,4-Dibromo-2,5-difluorobenzeneHCID 740491-Methyl-4-piperidoneHCID 178418339Butyllithium

Product 1

HCID 14770831HCID 14770831, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-75 °C

Procedure

A solution of 2.72 g (10 mmoles) of 1,4-dibromo-2,5-difluorobenzene in 50 ml of ethyl ether, under an argon atmosphere stirred at -75° C., was treated dropwise with 4.2 ml of 2.5 M n-butyl lithium (hexane solution). The mixture was treated dropwise with a solution of 1.20 g (10.6 mmoles) of N-methyl-4-piperidone in 10 ml of ethyl ether, stirred a further 0.75 hours at -75° C., let warm to -30° C., and poured into a solution of 0.56 g (10.5 mmoles) ammonium chloride in 15 ml of water. The ether layer was washed with two 10 ml portions of water, dried (MgSO4), and evaporated to give 2.85 g of crude product which was purified by chromatography on a column of silica gel and crystallized to give 1.30 g of the title compound; mp 133°-135° C.

Workup

  1. temperaturelet warm to -30° C.
  2. washThe ether layer was washed with two 10 ml portions of water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give 2.85 g of crude product which
  6. customwas purified by chromatography on a column of silica gel
  7. customcrystallized

Sources & evidence

ORD record
ord-cd70ae61f57c437c89bfa5bc977e6dae
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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