Potassium Carbonate → {1-[2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2-hydroxy-ethyl]-piperidin-4-yl}-(4-methoxy-benzothiazol-2-yl)-methanone

HRID 1012945Notes

Reaction equation

HRID 1012945 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[O:13])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[O:20]1[CH2:22][CH:21]1[C:23]1[CH:32]=[CH:31][C:26]2[O:27][CH2:28][CH2:29][O:30][C:25]=2[CH:24]=1.Cl([O-])(=O)(=O)=O.[Li+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:27]1[C:26]2[CH:31]=[CH:32][C:23]([CH:21]([OH:20])[CH2:22][N:17]3[CH2:18][CH2:19][CH:14]([C:12]([C:10]4[S:11][C:7]5[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=5[N:9]=4)=[O:13])[CH2:15][CH2:16]3)=[CH:24][C:25]=2[O:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 167813336-(Oxiran-2-yl)-2,3-dihydro-1,4-benzodioxineHCID 23665649Lithium perchlorateHCID 67315952(4-Methoxy-benzothiazol-2-yl)-piperidin-4-yl-methanone

Product 1

HCID 67316803{1-[2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2-hydroxy-ethyl]-piperidin-4-yl}-(4-methoxy-benzothiazol-2-yl)-methanoneYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (4-methoxy-benzothiazol-2-yl)-piperidin-4-yl-methanone (83 mg, 0.3 mmol), 6-oxiranyl-2,3-dihydro-benzo[1,4]dioxine (53.5 mg, 0.3 mmol), lithium perchlorate (32 mg, 0.3 mmol) and potassium carbonate (42 mg, 0.3 mmol) in DMF (2 ml) was heated at 80° C. overnight. The mixture was poured on water and extracted with EtOAc. Organic extracts were washed with water and brine, dried over MgSO4 and concentrated. Chromatography on SiO2 (EtOAc/MeOH 9:1) gave the title compound as a beige solid (100 mg, 73%, 4:1 mixture of regioisomers).

Workup

  1. additionThe mixture was poured on water
  2. extractionextracted with EtOAc
  3. washOrganic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-72d078c67fda4036aedb62b9acd30b08
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Reaction notes

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