Triethylamine → HCID 20148594, compound

HRID 569012Notes

Reaction equation

HRID 569012 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3].Cl.Cl.[NH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]1.C(N(CC)CC)C>O1CCCC1>[OH:29][CH:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][NH:20][S:2]([C:5]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:6]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3])[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13670189Methyl 2-(chlorosulfonyl)-6-nitrobenzoateHCID 140998861-(2-Aminoethyl)piperidin-4-ol--hydrogen chloride (1/2)

Product 1

HCID 20148594HCID 20148594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 2-chlorosulfonyl-6-nitrobenzoate (1.5 g, 5.4 mmol) in tetrahydrofuran (100 ml) was added over 1 hour to a stirred mixture of 1-(2-aminoethyl)-4-hydroxypiperidine dihydrochloride (1.2 g, 5.4 mmol) and triethylamine (2.3 ml, 16.5 mmol) in tetrahydrofuran (75 ml) cooled in an ice bath. After stirring at room temperature for 6 hours, solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium chloride solution. The ethyl acetate extract was dried (Na2SO4), filtered and concentrated. The residue was flash chromatographed on silica gel and eluted with 5% methanol-95% chloroform to give pure product, 1.0 g, as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. customsolvent was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and saturated sodium chloride solution
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel
  9. washeluted with 5% methanol-95% chloroform
  10. customto give pure product, 1.0 g

Sources & evidence

ORD record
ord-1e4627ed67714587b8a053d0416a57f1
Source dataset
uspto-grants-1988_03
Patent number
US04731369

Reaction notes

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