4-Piperidinecarboxylic acid → 1,1'-[Dithiobis(2,1-phenylenecarbonyl)]bis-4-piperidine carboxylic acid

HRID 583527

Reaction equation

HRID 583527 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.[CH3:10][N:11]([Si](C)(C)C)[C:12](=O)[CH3:13].[C:19](Cl)(=[O:37])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][S:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31]>N1C=CC=CC=1.ClCCl>[C:29]1([C:30]([N:11]2[CH2:12][CH2:13][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:10]2)=[O:31])[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=1[S:27][S:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)=[O:37]

Participants

6

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 81953N-Trimethylsilyl-N-methylacetamideHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 189352891,1'-[Dithiobis(2,1-phenylenecarbonyl)]bis-4-piperidine carboxylic acid

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Isonipecotic acid (4-piperidinecarboxylic acid) (0.76 g, 6 mmol), N-methyl-N-trimethylsilylacetamide and 3 drops of pyridine were stirred at room temperature for 2 hours. This suspension was added to a filtered solution of 2,2'-dithiobisbenzoyl chloride (1.0 g, 3.0 mmol) in 15 mL of dichloromethane. The solvent was removed after 18 hours and the residue was triturated with 1N HCl. The acid was decanted and the residue was dissolved in acetonitrile. After standing for 24 hours a precipitate formed. The solid was collected and dried to give 0.56 g of the title compound, mp >250° C.;

Workup

  1. customThe solvent was removed after 18 hours
  2. customthe residue was triturated with 1N HCl
  3. customThe acid was decanted
  4. dissolutionthe residue was dissolved in acetonitrile
  5. customa precipitate formed
  6. customThe solid was collected
  7. customdried

Sources & evidence

ORD record
ord-c61146ca283f4cb2a41cd703f4e7b458
Source dataset
uspto-grants-1999_07
Patent number
US05929114

Linked notes

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