Potassium Carbonate → HCID 15839395, compound

HRID 2292636Notes

Reaction equation

HRID 2292636 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.O[CH2:13][CH:14]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15]1.[O:22]1[C:27]2[CH:28]=[CH:29][C:30]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[CH:31][C:26]=2[O:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+]>C(C(C)=O)C(C)C>[CH:14]1([CH2:13][N:35]2[CH2:36][CH2:37][N:32]([C:30]3[CH:29]=[CH:28][C:27]4[O:22][CH2:23][CH2:24][O:25][C:26]=4[CH:31]=3)[CH2:33][CH2:34]2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10713381-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-piperazineHCID 85681027HCID 85681027, compound

Product 1

HCID 15839395HCID 15839395, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
100 °C

Procedure

2.26 g (7.8×10-3 mol) of 1-hydroxymethylbenzocyclobutane tosylate, 1.7 g (7.8×10-3 mol) of 4-(2,3-dihydrobenzo-1,4-dioxin-6-yl)piperazine and 2.16 g (15.6×10-3 mol) of K2CO3 in 50 ml of methyl isobutyl ketone are mixed together. That mixture is heated at 100° C. for 8 hours and then cooled. The mixture is concentrated and the residue is taken up in water and ethyl acetate. Separation is carried out and the organic phase then extracted with 1N HCl. The aqueous phase is rendered basic with 1N NaOH and then extracted with methylene chloride and dried over MgSO4. The oil obtained is purified by flash chromatography (eluant CH2Cl2/CH3OH: 95/5). 1 g (yield=38%) of an oil that corresponds to the title compound is obtained, the dihydrochloride of which is prepared in acetonitrile. M.p. 242°-245° C.

Workup

  1. temperaturecooled
  2. concentrationThe mixture is concentrated
  3. customSeparation
  4. extractionthe organic phase then extracted with 1N HCl
  5. extractionextracted with methylene chloride
  6. dry with materialdried over MgSO4
  7. customThe oil obtained
  8. customis purified by flash chromatography (eluant CH2Cl2/CH3OH: 95/5)

Sources & evidence

ORD record
ord-65060ccf9b0c46799fc1807fb8c30c5d
Source dataset
uspto-grants-1997_11
Patent number
US05684020

Reaction notes

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