Sodium Hydroxide → HCID 57966425, compound

HRID 420560Notes

Reaction equation

HRID 420560 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH2:15][C:16]4[CH:17]=[C:18]([O:23]C(=O)C)[CH:19]=[C:20]([CH3:22])[CH:21]=4)[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH2:15][C:16]4[CH:17]=[C:18]([OH:23])[CH:19]=[C:20]([CH3:22])[CH:21]=4)[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57966049HCID 57966049, compound

Product 1

HCID 57966425HCID 57966425, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of acetic acid 3-{[4-(6-chlorobenzothiazole-2-yl)piperazine-1-yl]methyl}-5-methylphenyl ester (1.97 g; 4.88 mmol), 2N-aqueous sodium hydroxide (10 ml) and methanol (20 ml) was stirred at 40° C. for 1 hour. The solvent was evaporated under reduced pressure. To the residue were added water and 2N-aqueous hydrochloric acid to be neutral. Ethyl acetate was added thereto 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 (ethyl acetate) to give 3-{[4-(6-chlorobenzothiazole-2-yl)piperazine-1-yl]methyl}-5-methylphenol as colorless amorphous solid (1.83 g; 100%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionTo the residue were added water and 2N-aqueous hydrochloric acid
  3. additionEthyl acetate was added
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatograph on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-de6ba88d185949469fbff5bc9404caad
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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