Potassium Carbonate → HCID 13747808, compound

HRID 329605Notes

Reaction equation

HRID 329605 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>>[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

4

Reactant 3

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

Product 1

HCID 13747808HCID 13747808, compound

Procedure

4.8 g 4-(4-(1,1-Dimethylethyl)-2-thiazolyl)-1-phenylmethyl-piperidine, 2 g K2CO3 and 50 ml 1,2-dicnloroethane 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 metnanol 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 etner 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 metnanol and 30 ml 20% aqueous hydrochloric acid
  5. temperatureThe mixture is heated 1 hour at 60
  6. customevaporated
  7. customThe residue is partitioned between aqueous NaOH and ether
  8. additionThe etner phase is treated with maleic acid

Sources & evidence

ORD record
ord-6f445d26b8b34db7932a6671a41c454a
Source dataset
uspto-grants-1990_01
Patent number
US04892879

Reaction notes

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