Pyridine → HCID 19775329, compound

HRID 1613183Notes

Reaction equation

HRID 1613183 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].Cl.Cl.NC[C:10]1[CH:36]=[CH:35][C:13]([CH2:14][N:15]([C:17]([CH3:34])([CH3:33])[CH2:18][O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:16])=[CH:12][CH:11]=1.[N:37]1C=CC=CC=1>>[ClH:5].[C:27]1([CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:19][CH2:18][C:17]([N:15]([CH2:14][C:13]2[CH:12]=[CH:11][C:10]([NH:37][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:36][CH:35]=2)[CH3:16])([CH3:33])[CH3:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 19775335HCID 19775335, compound

Product 1

HCID 19775329HCID 19775329, compound

Procedure

Methanesulphonyl chloride (40 μl) was added dropwise to a stirred solution of 2-[N-(4-aminomethylbenzyl)-N-methylamino]-1-diphenylmethoxy-2-methylpropane (140 mg -- see Example 46) in pyridine (5 ml) and the mixture was stirred at room temperature or 16 hours and evaporated. The residue was azeotroped twice with toluene, dissolved in 2M hydrochloric acid, washed with ether, basified with saturated aqueous sodium hydrogen carbonate solution and extracted into ethyl acetate. The organic extract was dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (3 g) using methylene chloride plus 0-5% methanol as the eluant. Appropriate fractions were combined and evaporated and the residue was dissolved in ether and treated with excess saturated ethereal hydrogen chloride. The resulting precipitated gum was collected and triturated with ether to give the title compound as a colourless solid which was characterised as a hemihydrate (31 mg, 17%), m.p. 150°-155°.

Workup

  1. customevaporated
  2. customThe residue was azeotroped twice with toluene
  3. dissolutiondissolved in 2M hydrochloric acid
  4. washwashed with ether
  5. extractionextracted into ethyl acetate
  6. extractionThe organic extract
  7. dry with materialwas dried over magnesium sulphate
  8. customevaporated
  9. customThe residue was purified by chromatography on silica (3 g)
  10. customevaporated
  11. dissolutionthe residue was dissolved in ether
  12. additiontreated with excess saturated ethereal hydrogen chloride
  13. customThe resulting precipitated gum
  14. customwas collected
  15. customtriturated with ether

Sources & evidence

ORD record
ord-a25aa75e53504a15b03f8923235bb02d
Source dataset
uspto-grants-1993_03
Patent number
US05192765

Reaction notes

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