Water → HCID 19375952, compound

HRID 1656413Notes

Reaction equation

HRID 1656413 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-854dde67b6094539a5e163af69b31382
Source dataset
uspto-grants-1993_10
Patent number
US05254575

Reaction notes

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