Triethylamine → HCID 18538909, compound

HRID 1394375Notes

Reaction equation

HRID 1394375 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31]([N:34]1[CH2:39][CH2:38][CH:37]([C:40]([Cl:42])=[O:41])[CH2:36][CH2:35]1)(=[O:33])[CH3:32].C([O-])(O)=O.[Na+]>CCOC(C)=O>[ClH:42].[C:31]([N:34]1[CH2:35][CH2:36][CH:37]([C:40]([N:17]([CH2:16][CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][CH:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:12]2)[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:41])[CH2:38][CH2:39]1)(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 516892Sodium BicarbonateHCID 22676614HCID 22676614, compound

Product 1

HCID 18538909HCID 18538909, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-[3-(4-Benzyl-1-piperidinyl)propyl]-3-pyridinamine (400 mg) in 6 ml of tetrahyfrofuran, triethylamine (0.719 ml) and 1-acetyl-4-piperidinecarbonyl chloride (180 mg) were added at 0° C., and the mixture was stirred for 2 h at 0° C. AcOEt (15 ml) and aq. NaHCO3 (15 ml) were added and the organic layer was separated. The aqueous layer was extracted with AcOEt (10 ml) twice. The combined AcOEt layer was washed with aq. NaHCO3 (10 ml) twice and brine (10 ml), dried over anhydrous MgSO4. After concentration, the residue was purified on Al2O3 column chromatography (hexane-AcOEt 1:1). After evaporation, to the residue 4N HCl in AcOEt (1.0 ml) was added and the resulting precipitate was collcted by filtration to give the title compound (251 mg, yield 39.0%).

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with AcOEt (10 ml) twice
  3. washThe combined AcOEt layer was washed with aq. NaHCO3 (10 ml) twice
  4. dry with materialbrine (10 ml), dried over anhydrous MgSO4
  5. concentrationAfter concentration
  6. customthe residue was purified on Al2O3 column chromatography (hexane-AcOEt 1:1)
  7. customAfter evaporation
  8. additionto the residue 4N HCl in AcOEt (1.0 ml) was added
  9. filtrationthe resulting precipitate was collcted by filtration

Sources & evidence

ORD record
ord-db6bb1244bff4215b2131231715b7ba8
Source dataset
uspto-grants-2008_03
Patent number
US07348324B2

Reaction notes

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