Triethylamine → HCID 19004214, compound

HRID 2225434Notes

Reaction equation

HRID 2225434 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].[NH2:6][C:7]1[CH:35]=[CH:34][C:10]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.C(N(CC)CC)C>O1CCOCC1>[ClH:5].[C:28]1([CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:20][CH2:19][CH:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][C:10]3[CH:9]=[CH:8][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:35][CH:34]=3)[CH2:14][CH2:15]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19004206HCID 19004206, compound

Product 1

HCID 19004214HCID 19004214, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methanesulphonyl chloride (69 mg, 0.60 mmol) was added dropwise to a stirred solution of 1-(4-aminophenethyl)-4-(diphenylmethoxymethyl)piperidine (200 mg, 0.50 mmol) (see Example 21) and triethylamine (61 mg, 0.60 mmol) in dioxane (5 ml) and the mixture heated under reflux for 2 hours and evaporated. The residue was partitioned between ethyl acetate and 10% aqueous potassium carbonate solution. The layers were separated and the aqueous layer extracted into ethyl acetate. The combined organic layers were dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-4% methanol as eluant. Appropriate fractions were combined and evaporated. The residue was dissolved in ether and the solution treated with excess ethereal hydrogen chloride. The mixture was decanted and the residual oil was washed with ether and dried to give the title compound (90 mg) as a pale yellow foam which was characterised containing 0.25 equivalents of water.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 hours
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and 10% aqueous potassium carbonate solution
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted into ethyl acetate
  7. dry with materialThe combined organic layers were dried over magnesium sulphate
  8. customevaporated
  9. customThe residue was purified by chromatography on silica
  10. customevaporated
  11. dissolutionThe residue was dissolved in ether
  12. additionthe solution treated with excess ethereal hydrogen chloride
  13. customThe mixture was decanted
  14. washthe residual oil was washed with ether
  15. customdried

Sources & evidence

ORD record
ord-a392ccb1a7314ce1afcf11ac0c429f98
Source dataset
uspto-grants-1994_09
Patent number
US05344835

Reaction notes

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