Sodium Hydroxide → HCID 19088503, compound

HRID 1463851Notes

Reaction equation

HRID 1463851 reaction equation
[CH2:1]([N:8]([C:10]([CH3:29])([CH3:28])[CH2:11][CH2:12][C:13]([C:26]#[N:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:30].[Na+]>S(=O)(=O)(O)O>[CH2:1]([N:8]([C:10]([CH3:29])([CH3:28])[CH2:11][CH2:12][C:13]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:26]([NH2:27])=[O:30])[CH3:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19088487HCID 19088487, compound

Product 1

HCID 19088503HCID 19088503, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-(N-benzyl-N-methylamino)-1-cyano-1,1-diphenyl-4-methylpentane (1.0 g--see Preparation 12) in 90% sulphuric acid (10 ml) was heated at 90° for 1 hour. The mixture was poured onto ice (100 g), basified to a pH of about 12 by the addition of 40% aqueous sodium hydroxide and extracted with dichloromethane (2×100 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 4%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a gum, yield 0.6 g.

Workup

  1. additionThe mixture was poured onto ice (100 g)
  2. extractionextracted with dichloromethane (2×100 ml)
  3. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a gum which
  6. customwas purified by column chromatography on silica eluting with dichloromethane
  7. additioncontaining methanol (0% up to 4%)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afec7888eac5477ea38098dee783b13a
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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