Potassium Carbonate → HCID 9906463, compound

HRID 2186806Notes

Reaction equation

HRID 2186806 reaction equation
C([NH:4][C:5]1[S:6][C:7]2[CH:13]=[C:12]([CH2:14][CH2:15]Br)[CH:11]=[CH:10][C:8]=2[N:9]=1)(=O)C.[CH2:17]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C(OC(=O)C)C>[NH2:4][C:5]1[S:6][C:7]2[CH:13]=[C:12]([CH2:14][CH2:15][N:27]3[CH2:28][CH2:29][CH:24]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:25][CH2:26]3)[CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 22449932HCID 22449932, compound

Product 1

HCID 9906463HCID 9906463, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3 g of 1-(2-Acetylamino-benzothiazol-6-yl)-2-bromo-ethane and 1.95 g of 4- benzylpiperidin and 3.5 g of K2CO3 in 20 ml of DME was heated at 75° C. for 2 hours. The solution was diluted with ethylacetate and washed with brine, after removal of the solvent the residue was heated at reflux in 50 ml of ethanol containing 5 ml of 5 M NaOH for 1 hour. The solvent was evaporated and the residue taken up in ethylacetate was washed with brine and dried. After removal of the solvent, the reaction produce was chromatographed on silica gel eluting with ethylacetate/cyclohexane ⅓ affording the title compound in 67% yield, m.p. 152-153° C.

Workup

  1. washwashed with brine
  2. customafter removal of the solvent the residue
  3. temperaturewas heated
  4. temperatureat reflux in 50 ml of ethanol containing 5 ml of 5 M NaOH for 1 hour
  5. customThe solvent was evaporated
  6. washwas washed with brine
  7. customdried
  8. customAfter removal of the solvent
  9. customthe reaction produce
  10. customwas chromatographed on silica gel eluting with ethylacetate/cyclohexane ⅓

Sources & evidence

ORD record
ord-6715b4f33fbd44bf9e7ae0f8db709b5f
Source dataset
uspto-grants-2002_06
Patent number
US06407122B1

Reaction notes

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