Potassium Carbonate → HCID 19970186, compound

HRID 974963Notes

Reaction equation

HRID 974963 reaction equation
Br.[Cl:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[CH2:15][C:16]([C:29]#[N:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-:34].[K+].[K+]>S(=O)(=O)(O)O>[C:29]([C:16]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:15][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][N:9]1[CH2:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([Cl:2])=[CH:32][CH:31]=1)(=[O:34])[NH2:30]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19970188HCID 19970188, compound

Product 1

HCID 19970186HCID 19970186, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-(4-chlorophenethyl)-2-(2-cyano-2,2-diphenylethyl)piperidine hydrobromide (Example 26) (122 mg, 0.24 mmol) in 90% sulphuric acid (2 ml) was stirred at 90° C. for 1.5 hours, diluted with ice, basified with excess solid potassium carbonate and extracted into dichloromethane. The combined dichloromethane extracts were dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-5% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (70 mg, 65%) as a colourless foam which was characterised as a dihydrate.

Workup

  1. additiondiluted with ice
  2. extractionextracted into dichloromethane
  3. dry with materialThe combined dichloromethane extracts were dried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by chromatography on silica
  6. customevaporated

Sources & evidence

ORD record
ord-549cfb2caeed42d3a6afa226e0f6f0cb
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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