Triethylamine → HCID 15229595, compound

HRID 1034416Notes

Reaction equation

HRID 1034416 reaction equation
C1(C)C=CC(S([O:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])(=O)=O)=CC=1.[C:22]([N:30]1[CH2:35][CH2:34][CH:33]([CH2:36][CH2:37]O)[CH2:32][CH2:31]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:22]([N:30]1[CH2:35][CH2:34][CH:33]([CH2:36][CH2:37][O:10][S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)(=[O:12])=[O:13])[CH2:32][CH2:31]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77773Toluene-p-sulphonic anhydrideHCID 104214984-Piperidineethanol, 1-benzoyl-

Product 1

HCID 15229595HCID 15229595, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of p-toluene sulfonic anhydride (6.0 g, 18 mmol) in dichloromethane (50 mL) was added dropwise over 1 hour to a room temperature solution of 1-benzoyl-4-hydroxyethylpiperidine (4.3 g, 18 mmol) and dry triethylamine (2.8 mL, 2 mmol) in dichloromethane. After 2 hours, the mixture was diluted with ethyl acetate (500 mL) and extracted successively with H2O (2 ×100 mL), cold 0.1 M aqueous HCl (100 mL), saturated aqueous NaHCO3 (100 mL), and brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by chromatography on silica gel, eluting with ethyl acetate, and concentrated to yield a crystalline solid (6.2 g, 89%) which melted at 81°-83° C. Analysis: Calculated for C21H25NO4S: C,65.09; H,6.50; N,3.61; S,8.27; found: C.,65.31; H,6.74; N,3.41; S,8.30.

Workup

  1. extractionextracted successively with H2O (2 ×100 mL), cold 0.1 M aqueous HCl (100 mL), saturated aqueous NaHCO3 (100 mL), and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography on silica gel
  6. washeluting with ethyl acetate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-876f9b564e044606a553d54df876f9f5
Source dataset
uspto-grants-1994_05
Patent number
US05317024

Reaction notes

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