Lithium Hydroxide → HCID 66658000, compound

HRID 420563Notes

Reaction equation

HRID 420563 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22]C(=O)C)=[CH:18][CH:17]=4)[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.[OH-].[Li+].[C:30]([O:33][CH2:34][CH2:35]Br)(=[O:32])[CH3:31].C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.O.CN(C)C=O.C1COCC1>[C:30]([O:33][CH2:34][CH2:35][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:12]2[CH2:13][CH2:14][N:9]([C:7]3[S:8][C:4]4[CH:3]=[C:2]([Cl:1])[CH:27]=[CH:26][C:5]=4[N:6]=3)[CH2:10][CH2:11]2)=[CH:17][CH:18]=1)(=[O:32])[CH3:31]

Participants

9

Reactant 4

HCID 3939Lithium HydroxideHCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 57966434HCID 57966434, compound

Product 1

HCID 66658000HCID 66658000, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of acetic acid 4-{[4-(6-chlorobenzothiazole-2-yl)piperazine-1-yl]methyl}phenyl ester (0.33 g; 0.834 mmol), lithium hydroxide (0.04 g; 0.831 mmol) and THF (8 ml) was stirred at room temperature for 5 hours. The solvent was evaporated under reduced pressure. To the residue were added bromoethyl acetate (0.14 ml; 1.26 mmol), cesium carbonate (0.41 g; 1.26 mmol) and anhydrous N,N-dimethylformamide (4 ml). The mixture was stirred at room temperature for 17 hours. Water and ethyl acetate were added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=2:1) to give 4-{[4-(6-chlorobenzothiazole-2-yl)piperazine-1-yl]methyl}phenoxyethyl acetate as colorless oil (0.35 g; 93%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. stirringThe mixture was stirred at room temperature for 17 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatograph on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-c8c77d7271a64d26876016d5b4df29d0
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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