Potassium Carbonate → HCID 50852345, compound

HRID 1637174Notes

Reaction equation

HRID 1637174 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].CS(O[CH2:23][CH2:24][CH:25]=[C:26]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[CH2:30][CH2:29][C:28]2[CH:37]=[CH:38][CH:39]=[CH:40][C:27]1=2)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:12]2[CH2:13][CH2:14][N:15]([CH2:23][CH2:24][CH:25]=[C:26]3[C:27]4[CH:40]=[CH:39][CH:38]=[CH:37][C:28]=4[CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]3=4)[CH2:16][CH2:17]2)=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1712712HCID 1712712, compoundHCID 11615598ethyl 2-(piperazin-1-yl)nicotinate

Product 1

HCID 50852345HCID 50852345, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(1-piperazinyl)-3-pyridinecarboxylic acid ethyl ester (4.6 g, 0.019 mol), 3-(10,11 -dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl methanesulfonate (5.0 g, 0.015 mol) and potassium carbonate (4.8 g) in N,N-dimethylformamide (50 ml) was heated to 60° .C for 5 h. After standing overnight, the solid was filtered off and washed with benzene. The filtrate was diluted with benzene (200 ml) and washed with water (4×100 ml). The organic solution was dried (MgSO4) and the solvent evaporated in vacuo. The residue (7.8 g) was purified by column chromatography on silica gel using benzene and a benzene-ethyl acetate mixture as eluents, affording 2-(4-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene) -1-propyl)-1-piperazinyl)-3-pyridinecarboxylic acid ethyl ester (3.4 g, 48%) as an oil.

Workup

  1. temperaturewas heated to 60° .C for 5 h
  2. filtrationthe solid was filtered off
  3. washwashed with benzene
  4. additionThe filtrate was diluted with benzene (200 ml)
  5. washwashed with water (4×100 ml)
  6. dry with materialThe organic solution was dried (MgSO4)
  7. customthe solvent evaporated in vacuo
  8. customThe residue (7.8 g) was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-42f7c09911d14680a94142441bfc6660
Source dataset
uspto-grants-2000_03
Patent number
US06040302

Reaction notes

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