HCID 59605970, compound → (4-Methylpiperidin-4-yl)(pyrrolidin-1-yl)methanone

HRID 1945493Notes

Reaction equation

HRID 1945493 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH3:21])([C:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl.O>[CH3:21][C:11]1([C:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 1

HCID 59605970HCID 59605970, compound

Product 1

HCID 24728852(4-Methylpiperidin-4-yl)(pyrrolidin-1-yl)methanoneYield 99.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-methyl-4-(pyrrolidine-1-carbonyl)piperidine-1-carboxylic acid tert-butyl ester (296 mg, 1.0 mmol) in TFA (5 mL), DCM (5 mL) and water (0.1 mL) was stirred at room temperature for 2 hours and then concentrated under reduced pressure. The residue was taken up in MeOH and loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was washed with MeOH and the desired product was eluted with 2M NH3 in MeOH. The solvents were removed to give the desired product as a white solid (196 mg, 66%). LCMS (Method A): RT 0.31 min; [M+H]+ 197

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe cartridge was washed with MeOH
  3. washthe desired product was eluted with 2M NH3 in MeOH
  4. customThe solvents were removed

Sources & evidence

ORD record
ord-e9fa50f03ccb4474a83d7c8d5b11b311
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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