Sodium Carbonate → HCID 70004001, compound

HRID 580903

Reaction equation

HRID 580903 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH2:3][CH2:2]1.Cl[CH2:17][CH2:18][C:19]1[C:24](=[O:25])[N:23]2[CH:26]=[CH:27][S:28][C:22]2=[N:21][C:20]=1[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CC(=O)C.[I-].[K+]>[N:7]1([CH:4]2[CH2:5][CH2:6][N:1]([CH2:17][CH2:18][C:19]3[C:24](=[O:25])[N:23]4[CH:26]=[CH:27][S:28][C:22]4=[N:21][C:20]=3[CH3:29])[CH2:2][CH2:3]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 8178726-(2-chloroethyl)-7-methyl-5H-(1,3)thiazolo(3,2-a)pyrimidin-5-oneHCID 140907551-(Piperidin-4-yl)-1H-indole

Product 1

HCID 70004001HCID 70004001, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1-(4-piperidinyl)-1H-indole (4.1 g), 6-(2-chloroethyl)-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one (3.4 g), prepared as described in EP-A-0,196,132, sodium carbonate (6 g) and potassium iodide (0.1 g) in 4-methyl-2-pentanone (250 ml) was stirred and refluxed overnight. The warm reaction mixture was filtered and the filtrate was evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2 /C2H5OH 90/10). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from DIPE with a small amount of CH3CN. The precipitate was filtered off and dried, yielding 3 g (51%) 6-[2-[4-(1H-indol-1-yl)-1-piperidinyl]ethyl]-7-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one (compound 3; mp. 134.4° C.).

Workup

  1. customprepared
  2. temperaturerefluxed overnight
  3. customThe warm reaction mixture
  4. filtrationwas filtered
  5. customthe filtrate was evaporated
  6. customThe residue was purified over silica gel on a glass
  7. filtrationfilter (eluent: CH2Cl2 /C2H5OH 90/10)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue was crystallized from DIPE with a small amount of CH3CN
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-eb63fc27d2a94fc989572b3e79e0be3c
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Linked notes

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