Potassium Carbonate → HCID 13747808, compound

HRID 648942Notes

Reaction equation

HRID 648942 reaction equation
[CH3:1][C:2]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:15][CH2:14][N:13](CC3C=CC=CC=3)[CH2:12][CH2:11]2)[S:8][CH:9]=1)([CH3:4])[CH3:3].C([O-])([O-])=O.[K+].[K+].C(OC(Cl)=O)=C>ClCCCl>[CH3:4][C:2]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[S:8][CH:9]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78808Vinyl chloroformateHCID 13747807HCID 13747807, compound

Product 1

HCID 13747808HCID 13747808, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4.8 g 4-(4-(1,1-Dimethylethyl)-2-thiazolyl)-1-phenylmethyl-piperidine, 2 g K2CO3 and 50 ml 1,2-dichloroethane are treated dropwise at -5° under stirring with 3.2 g chloroformic acid vinyl ester. The mixture is stirred 2 hours at room temperature and evaporated. The residue is partitioned between ethyl ether and water. The ether phase is evaporated and the residue dissolved in 30 ml methanol and 30 ml 20% aqueous hydrochloric acid. The mixture is heated 1 hour at 60° and evaporated. The residue is partitioned between aqueous NaOH and ether. The ether phase is treated with maleic acid to yield the hydrogenmaleinate of the title compound, m.p. 141°-142° (ethanol/ether).

Workup

  1. customevaporated
  2. customThe residue is partitioned between ethyl ether and water
  3. customThe ether phase is evaporated
  4. dissolutionthe residue dissolved in 30 ml methanol
  5. temperatureThe mixture is heated 1 hour at 60°
  6. customevaporated
  7. customThe residue is partitioned between aqueous NaOH and ether
  8. additionThe ether phase is treated with maleic acid

Sources & evidence

ORD record
ord-62a1e76044914227b82b49ec3c9f9e6f
Source dataset
uspto-grants-1988_04
Patent number
US04737500

Reaction notes

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