Ammonium Chloride → HCID 68527050, compound

HRID 884169Notes

Reaction equation

HRID 884169 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:23])[C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][C:47](=[O:50])[CH2:46][CH2:45]1)=[O:43])([CH3:40])([CH3:39])[CH3:38].[Cl-].[NH4+]>C1COCC1>[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][C:47]([C:2]2[CH:25]=[CH:24][C:5]([O:6][C:7]3[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:23])[C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=4)=[CH:9][CH:8]=3)=[CH:4][CH:3]=2)([OH:50])[CH2:46][CH2:45]1)=[O:43])([CH3:40])([CH3:38])[CH3:39]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 68525867HCID 68525867, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 68527050HCID 68527050, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-[4-(4-bromophenoxy)phenyl]-3,4-dichlorobenzamide (4.94 g, 11.3 mmol) in THF (100 mL) was stirred at −85° C., and added a solution of 2.46 M n-butyl lithium hexane (9.65 mL, 23.7 mmol) dropwise over 10 minutes. Upon stirring for 20 minutes at the same temperature, crystals were precipitated. To this reaction solution was added a solution of 1-(t-butoxycarbonyl)-4-piperidone (2.48 g, 12.4 mmol) in THF (20 mL). The temperature of the solution was raised over 3 hours to −40° C., and then aqueous saturated ammonium chloride was added to the solution. The resulting reaction solution was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was then evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:3 to 1:1), to yield 2.30 g of a white powder. These crystals were washed with ether, to thereby yield 1.80 g of the title compound.

Workup

  1. customwere precipitated
  2. temperatureThe temperature of the solution was raised over 3 hours to −40° C.
  3. customThe resulting reaction solution
  4. extractionwas extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then evaporated
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:3 to 1:1)

Sources & evidence

ORD record
ord-cccf37f998a541039a5a6fd4d318ab74
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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