Pyridine → Methyl 3-[4-(5-methylpyridin-2-yl)aminopiperidin-1-ylmethyl]tricyclo[3.3.1.13,7]decane--1-carboxylate

HRID 1820305Notes

Reaction equation

HRID 1820305 reaction equation
O[CH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([C:13]([O:15][CH3:16])=[O:14])([CH2:6]3)[CH2:4]1)[CH2:10]2.N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:38][C:39]1[CH:40]=[CH:41][C:42]([NH:45][CH:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)=[N:43][CH:44]=1>C(Cl)Cl.O>[CH3:38][C:39]1[CH:40]=[CH:41][C:42]([NH:45][CH:46]2[CH2:51][CH2:50][N:49]([CH2:10][C:9]34[CH2:2][CH:3]5[CH2:12][CH:7]([CH2:6][C:5]([C:13]([O:15][CH3:16])=[O:14])([CH2:4]5)[CH2:11]3)[CH2:8]4)[CH2:48][CH2:47]2)=[N:43][CH:44]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 18410517Methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylateHCID 230210485-Methyl-N-(piperidin-4-YL)pyridin-2-amine

Product 1

HCID 23109891Methyl 3-[4-(5-methylpyridin-2-yl)aminopiperidin-1-ylmethyl]tricyclo[3.3.1.13,7]decane--1-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

After dissolving methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylate (0.1648 g, 0.735 mmol) and pyridine (0.0829 g, 1.05 mmol) in methylene chloride (5 mL), trifluoromethanesulfonic anhydride (0.185 mL, 1.11 mmol) was added dropwise while cooling on ice and the mixture was stirred for 1 hour. Water (10 mL) was added to the reaction mixture, and after extraction with ethyl acetate (20 mL), the extract was washed with 1N HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (10 mL) in that order and dried over anhydrous magnesium sulfate, and then 4-(5-methylpyridin-2-yl)aminopiperidine (0.2995 g, 1.57 mmol) was mixed therewith and the solvent was distilled off under reduced pressure. The obtained yellow oil was heated at 60° C. for 1 hour. It was then subjected to chromatography (50 g Merck Art. 9385, methylene chloride:methanol:ammonia water=97:3:0.2) to obtain the title compound as a white solid (0.2398 g, 0.603 mmole) (82% yield).

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling on ice
  3. extractionafter extraction with ethyl acetate (20 mL)
  4. washthe extract was washed with 1N HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (10 mL) in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f040a2d2832f4304ab912427de10da89
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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