Dimethylformamide → HCID 66657888, compound

HRID 420599Notes

Reaction equation

HRID 420599 reaction equation
[N:1]1([C:6]2([CH2:12][CH2:13][OH:14])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:16]1[S:17][C:18]([Br:21])=[CH:19][N:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:21][C:18]1[S:17][C:16]([N:9]2[CH2:8][CH2:7][C:6]([CH2:12][CH2:13][OH:14])([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH2:11][CH2:10]2)=[N:20][CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3123942,5-DibromothiazoleHCID 579662072-(4-Pyrrolidine-1-ylpiperidine-4-yl)ethanol

Product 1

HCID 66657888HCID 66657888, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(4-pyrrolidine-1-ylpiperidine-4-yl)ethanol (4.11 g), 2,5-dibromothiazole (5.03 g), potassium carbonate (3.43 g) and dimethylformamide (75 mL) was stirred at 60° C. for 16 hours. To the reaction solution was added water and extracted with ethyl acetate. The organic layer was washed with water and brine, and washed with magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (3.88 g). Yield: 52%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. washwashed with magnesium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-db31f221e63c4362aec46158cc7a48bd
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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