4-Piperidinecarboxylic acid → HCID 14127467, compound

HRID 648923Notes

Reaction equation

HRID 648923 reaction equation
CN(C)C=O.[Cl:6]([O-:10])(=[O:9])(=[O:8])=[O:7].CS[C:13]1[S:17][CH:16]=[CH:15][S+:14]=1.[NH:18]1[CH2:26][CH2:25][CH:21]([C:22]([OH:24])=[O:23])[CH2:20][CH2:19]1.C(OCC)(=O)C>CC(C)=O.C(OCC)C>[Cl:6]([O-:10])(=[O:9])(=[O:8])=[O:7].[S:14]1[CH:15]=[CH:16][S:17][C:13]1=[N+:18]1[CH2:26][CH2:25][CH:21]([C:22]([OH:24])=[O:23])[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 37734-Piperidinecarboxylic acidHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 230390092-Methylthio-1,3-dithiolium perchlorate

Product 1

HCID 14127467HCID 14127467, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 21584533Acetone diethyletherSolvent

Procedure

To 5 ml of dimethylformamide, 2.0 g of 2-methylthio-1,3-dithiolium perchlorate was suspended, and 1.2 g of isonipecotic acid was gradually added thereto under stirring at room temperature. The mixture was stirred at room temperature for 1 hour, and after an addition of 60 ml of ethyl acetate, the precipitated crystals were collected by filtration and recrystallized from acetone-ethyl ether, whereby 1.6 g (yield: 61%) of 1-(1,3-dithiol-2-ylidene)-4-carboxypiperidinium perchlorate (Compound No. 57) was obtained as crystals having a melting point of from 170° to 172° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-a7734b5ede904ab6a63aaee07b42a0df
Source dataset
uspto-grants-1988_04
Patent number
US04737494

Reaction notes

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