Benzene → HCID 50851740, compound

HRID 1107268Notes

Reaction equation

HRID 1107268 reaction equation
Br[CH2:2][CH2:3][O:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][C:8]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:7]=2[CH2:6]1.[CH2:21]([O:23][C:24]([CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])[CH3:22].C(=O)([O-])[O-].[K+].[K+].C1C=CC=CC=1>CN(C)C=O.O>[CH2:21]([O:23][C:24]([CH:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][O:4][CH:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][C:8]3[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:7]=3[CH2:6]2)[CH2:28][CH2:27]1)=[O:25])[CH3:22]

Participants

7

Reactant 4

HCID 241BenzeneHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 14248804HCID 14248804, compound

Product 1

HCID 50851740HCID 50851740, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
63 °C

Procedure

A mixture of 10-(2-bromoethoxy)-2-chloro-10,11-dihydrodibenzo[b,f]thiepine (5.19 g, 14 mmol, prepared similarly as described in example 2), 4-piperidinecarboxylic acid ethyl ester (2.20 g, 14 mmol) and anhydrous potassium carbonate (4.70 g, 34 mmol) in dry N,N-dimethylformamide (25 ml) was stirred at 60-66° C. for 6 h. After standing overnight at room temperature, benzene (50 ml) and water (50 ml) were added, and the phases were separated. The organic layer was washed with water (2×50 ml), dried (K2CO3) and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel using benzene as eluent, affording 4.28 g (68%) of oily 1-(2-(2-chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yloxy)-1-ethyl)-4-piperidinecarboxylic acid ethyl ester. The oil was dissolved in dry acetone (40 ml), oxalic acid dihydrate (1.76 g, 14 mmol) and ether were added, and the formed hydrogen oxalate was crystallised from a mixture of acetone and ether.

Workup

  1. customprepared similarly
  2. waitAfter standing overnight at room temperature
  3. customthe phases were separated
  4. washThe organic layer was washed with water (2×50 ml)
  5. dry with materialdried (K2CO3)
  6. customevaporated in vacuo
  7. customThe oily residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0e368d32a5374849bccd870a8075f667
Source dataset
uspto-grants-2000_05
Patent number
US06060468

Reaction notes

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