Triethylamine → 3-[2-(N-Boc-Piperidin-4-yl)ethylaminosulfonyl]benzoic Acid

HRID 265861Notes

Reaction equation

HRID 265861 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.Cl[S:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([OH:33])=[O:32])(=[O:27])=[O:26]>C(Cl)(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][S:25]([C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)[C:31]([OH:33])=[O:32])(=[O:27])=[O:26])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

Product 1

HCID 190341623-[2-(N-Boc-Piperidin-4-yl)ethylaminosulfonyl]benzoic Acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(N-Boc-4-piperidinyl)ethyl-amine (1-6) (0.45 g, 2.0 mmoles) in CHCl3 (20 ml) was treated with added triethylamine (0.405 g, 4.0 mmoles) followed by 3-chlorosulfonylbenzoyl chloride (3-1) (0.44 g, 2.0 mmoles) and the resulting solution was stirred at room temperature for 16 hours. The solvent was then removed and the residue was taken up in EtOAc and washed with H2O, 10% KHSO4 solution, brine and dried (Na2SO4). Solvent removal provided a residue that was purified by flash chromatography on silica gel eluting with CHCl3 (95)/MeOH(5) to give pure 4-1.

Workup

  1. customThe solvent was then removed
  2. washwashed with H2O, 10% KHSO4 solution, brine
  3. dry with materialdried (Na2SO4)
  4. customSolvent removal
  5. customprovided a residue that
  6. customwas purified by flash chromatography on silica gel eluting with CHCl3 (95)/MeOH(5)
  7. customto give pure 4-1

Sources & evidence

ORD record
ord-b8cfed57af6547d7841db1e7028c3020
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

Loading…