Triethylamine → HCID 18538909, compound

HRID 412951Notes

Reaction equation

HRID 412951 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-28ed75baab4743faa570b6a0ee0a880a
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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