Ammonium Chloride → (E)-3-[(Pyrrol-2-yl)methylidene]-1-(triphenylmethyl)piperidin-4-one

HRID 1171657Notes

Reaction equation

HRID 1171657 reaction equation
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(OC([N:44]1[CH:48]=[CH:47][CH:46]=[C:45]1[CH:49]=O)=O)(C)(C)C.[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[NH:44]1[CH:48]=[CH:47][CH:46]=[C:45]1/[CH:49]=[C:10]1\[CH2:9][N:8]([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:13][CH2:12][C:11]\1=[O:14]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 27484141-Tritylpiperidin-4-oneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 5057005tert-Butyl 2-formyl-1H-pyrrole-1-carboxylate

Product 1

HCID 23138769(E)-3-[(Pyrrol-2-yl)methylidene]-1-(triphenylmethyl)piperidin-4-oneYield 35%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(triphenylmethyl)piperidin-4-one (17.00 g) in tetrahydrofuran (400 ml) was added dropwise a 0.5N solution of potassium bis(trimethylsilyl)amide in toluene (100 ml) at −70° C., and the resulting mixture was stirred at the same temperature for 20 minutes. Subsequently, to the reaction mixture was added dropwise a solution of 1-(t-butoxycarbonyl)pyrrole-2-carbaldehyde (11.00 g) in tetrahydrofuran (100 ml) at −70° C., and the resulting mixture was stirred at the same temperature for 1 hour. After saturated aqueous ammonium chloride solution was added, the resulting reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate, hexane, and dichloromethane (1:3:1) as the eluent to afford the title compound (7.26 g, yield: 35%) as a yellow amorphous solid.

Workup

  1. stirringthe resulting mixture was stirred at the same temperature for 1 hour
  2. customthe resulting reaction mixture
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-c8197e42b60344b9ba78b7da8b756cb7
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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