Diisopropylethylamine → HCID 66799234, compound

HRID 1193406Notes

Reaction equation

HRID 1193406 reaction equation
[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.Br[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C>C(O)CCC>[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 881004-Bromopyridinium chlorideHCID 44829085Phenylmethyl N-methyl-N-3-piperidinylcarbamate

Product 1

HCID 66799234HCID 66799234, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of benzyl methyl(piperidin-3-yl)carbamate (6.32 mmol, 1.0 eq.), 4-brompyridine HCl (2.5 g, 12.64 mmol, 2.0 eq.) and DIPEA (5.7 ml, 31.6 mmol, 5.0 eq.) in n-butanol (40 ml) was refluxed for 24 hours. The reaction mixture was concentrated and the residue was taken up in DCM (200 ml) and washed with sat. NaHCO3 solution (3×100 ml), water (100 ml) and sat. NaCl solution (100 ml). The org. phase was then dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 5% MeOH in DCM). Yield: 77% (1.6 g, 4.92 mmol)

Workup

  1. temperaturewas refluxed for 24 hours
  2. concentrationThe reaction mixture was concentrated
  3. washwashed with sat. NaHCO3 solution (3×100 ml), water (100 ml) and sat. NaCl solution (100 ml)
  4. dry with materialphase was then dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography (silica gel, 5% MeOH in DCM)

Sources & evidence

ORD record
ord-e193ba89e51748029f013ffef217c73f
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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