Dimethylformamide → 1-(6-Chloro-2-benzothiazolyl)-4-piperidineethanol

HRID 420557Notes

Reaction equation

HRID 420557 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][OH:20])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.O>[Cl:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][OH:20])[CH2:14][CH2:13]3)[S:3][C:4]=2[CH:10]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 739534-PiperidineethanolHCID 771762,6-Dichlorobenzothiazole

Product 1

HCID 579661101-(6-Chloro-2-benzothiazolyl)-4-piperidineethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,6-dichlorobenzothiazole (3.00 g; 14.7 mmol), 4-piperidine ethanol (2.09 g; 16.2 mmol), potassium carbonate (2.33 g; 16.2 mmol) and anhydrous N,N-dimethylformamide (15 ml) was stirred at room temperature for 16 hours. Water and ethyl acetate were added to the reaction solution. The organic layer was separated, washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The precipitate was washed with diisopropyl ether to give 6-chloro-2-[4-(2-hydroxyethyl)piperidine-1-yl]benzothiazole as green crystal (2.92 g; 67%).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure
  5. washThe precipitate was washed with diisopropyl ether

Sources & evidence

ORD record
ord-f838d809cc8445b28073cbdba37e578e
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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