Dimethylformamide → HCID 66865062, compound

HRID 222583Notes

Reaction equation

HRID 222583 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][N:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([CH:31](OS(C)(=O)=O)C)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31][O:17][C:14]2[CH:15]=[CH:16][C:11]([C:8]3[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH2:6][CH:7]=3)=[N:12][CH:13]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 232828864-[1-[(Methylsulfonyl)oxy]ethyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl esterHCID 66865178HCID 66865178, compound

Product 1

HCID 66865062HCID 66865062, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 3-necked flask is added 1′-methanesulfonyl-1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl-5-ol (254.3 g, 1.0 mol) followed by 4-(1-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (396.1 g,1.34 mol) and potassium carbonate (248.8 g, 1.8 mol). Dimethylformamide (3800 mL) is added and the mixture is heated at 80˜90° C. for 6 h. 3810 mL of water are added dropwise at 70˜80° C. The mixture is cooled slowly to 20˜30° C. and filtered. The cake is slurried with 1000 mL of water, concentrated and dried under vacuum to provide 407 g of a solid with 97.13% HPLC purity.

Workup

  1. temperaturethe mixture is heated at 80˜90° C. for 6 h
  2. temperatureThe mixture is cooled slowly to 20˜30° C.
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0c433fa4c48244708c65588633b55ae1
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

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