Water → HCID 69562634, compound

HRID 1837755Notes

Reaction equation

HRID 1837755 reaction equation
[O:1]=[C:2]1[C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=CN=2)=[CH:6][CH:5]=[CH:4][NH:3]1.Br[CH2:25][CH:26]1[CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+].O.[CH3:36][N:37](C)C=O>>[O:1]=[C:2]1[C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[CH2:15][CH2:16][CH2:17][C:18]2[CH:36]=[N:37][CH:21]=[CH:22][CH:23]=2)=[CH:6][CH:5]=[CH:4][N:3]1[CH2:25][CH:26]1[CH2:28][CH2:27]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 22678450HCID 22678450, compound

Product 1

HCID 69562634HCID 69562634, compound

Conditions

Temperature
80 °C

Procedure

300 mg of 1-[(2-Oxo-1,2-dihydro-3-pyridinyl)methyl]-2-[3-(2-pyridyl)propyl]piperidine obtained in Example 178, 0.2 ml of (bromomethyl)cyclopropane and 610 mg of potassium carbonate were suspended in 5 ml of N,N-dimethylformamide (DMF), and the mixture were stirred at 80° C. for 4 hours. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate. The drying agent was filtered off, and the solvent was evaporated. The residue was purified by NH-silica gel column chromatography (hexane:ethyl acetate=2:1, subsequently 1:1, and subsequently ethyl acetate), to give 150 mg of the objective oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate
  3. filtrationThe drying agent was filtered off
  4. customthe solvent was evaporated
  5. customThe residue was purified by NH-silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-8bb8106b9f484ae1b5405a12025ac34c
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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