Potassium Carbonate → HCID 69948095, compound

HRID 612445Notes

Reaction equation

HRID 612445 reaction equation
Br[CH2:2][CH:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][S:7][C:6]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:5]1=2.[C:20](=[O:23])([O-:22])[O-].[K+].[K+].[CH2:26]([O:28][C:29]([CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])[CH3:27]>CN(C)C=O.ClCCl>[C:29]([OH:30])(=[O:28])[C:20]([OH:22])=[O:23].[CH2:26]([O:28][C:29]([CH:31]1[CH2:36][CH2:35][N:34]([CH2:2][CH:3]=[C:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][S:7][C:6]3[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:5]2=3)[CH2:33][CH2:32]1)=[O:30])[CH3:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 54203531HCID 54203531, compound

Product 1

HCID 69948095HCID 69948095, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 11-(2-bromoethylidene)-2-chloro-6,11-dihydrodibenzo[b,e]thiepine (1.76 g, 0.005 mol, prepared as described in Example 3) in N,N-dimethylformamide (20 ml), potassium carbonate (2.33, 0.006 mol) and 4-piperidinecarboxylic acid ethyl ester (0.86 g, 0.0055 mol) were added and the mixture was stirred at 50° C. for 3 h. The reaction mixture was diluted with dichloromethane (80 ml), the solid was filtered off and the filtrate was washed with water (4×30 ml). The dichloromethane solution was dried (MgSO4) and the solvent removed in vacuo. The oily residue (2.34 g) was dissolved in acetone and treated with an ethanolic solution of oxalic acid. The precipitated crude hydrogen oxalate salt (5.8 g) was recrystalised from aqueous ethanol, to give 1.12 g (87%) of 1-(2-(2-chloro-6,11-dihydrodibenzo[b,e]thiepin-11-ylidene)-1-ethyl)-4-piperidinecarboxylic acid ethyl ester hydrogen oxalate.

Workup

  1. filtrationthe solid was filtered off
  2. washthe filtrate was washed with water (4×30 ml)
  3. dry with materialThe dichloromethane solution was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. dissolutionThe oily residue (2.34 g) was dissolved in acetone
  6. additiontreated with an ethanolic solution of oxalic acid
  7. customThe precipitated crude hydrogen oxalate salt (5.8 g)
  8. customwas recrystalised from aqueous ethanol

Sources & evidence

ORD record
ord-44fb896d14064895895139b2cc2f1335
Source dataset
uspto-grants-1999_12
Patent number
US06004983

Reaction notes

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