Sodium Carbonate → HCID 19970196, compound

HRID 974964Notes

Reaction equation

HRID 974964 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([C:28]#[N:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:31].[Na+].[Na+]>S(=O)(=O)(O)O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([C:28](=[O:31])[NH2:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 199701931-Benzyl-4-(2-cyano-2,2-diphenylethyl)piperidine

Product 1

HCID 19970196HCID 19970196, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-benzyl-4-(2-cyano-2,2-diphenylethyl)piperidine (7.57 g, 19.9 mmol) (Example 23) in 90% sulphuric acid (45 ml) was heated at 100° C. for one hour, allowed to cool to room temperature, poured into ice, basified with saturated aqueous sodium carbonate solution and extracted into dichloromethane. The combined organic extracts were dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-10% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (1.06 g, 13%) as a colourless foam which was characterised as a hemihydrate.

Workup

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

Sources & evidence

ORD record
ord-6ff51a03010746eca1233d122640b4a2
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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