Water → HCID 19375952, compound

HRID 2211159Notes

Reaction equation

HRID 2211159 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]#[N:14])[S:11][CH:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.O>CN(C)C=O>[N:25]1([CH2:24][CH2:23][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:9]=[C:10]([C:13]#[N:14])[S:11][CH:12]=3)=[CH:6][CH:7]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 19375965HCID 19375965, compound

Product 1

HCID 19375952HCID 19375952, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-(4-hydroxyphenyl)-thiazole-2-carbonitrile (7 g), crushed potassium carbonate (13.1 g) and 1-(2-chloroethyl)piperidine hydrochloride (7.78 g) in dry dimethylformamide (60 ml) was stirred at room temperature for 28 h, and then added to water (400 ml). The precipitated solid was filtered, and then partitioned between dichloromethane and water. The organic layer was dried over sodium sulphate, filtered, and evaporated to dryness to give 4-[4-[2-(piperidin-1-yl)ethyloxy]phenyl]-thiazole-2-carbonitrile (10.1 g), m.p. 85°-86° C.

Workup

  1. filtrationThe precipitated solid was filtered
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-76b8c0fff5314ac5b88cae64e36111d3
Source dataset
uspto-grants-1995_10
Patent number
US05462959

Reaction notes

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