2-Bromothiazole → HCID 14022497, compound

HRID 1710082Notes

Reaction equation

HRID 1710082 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:20]1[S:21][CH:22]=[CH:23][N:24]=1>N1C=CC=CC=1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:20]2[S:21][CH:22]=[CH:23][N:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 764302-BromothiazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 14022497HCID 14022497, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (7.45 g) and 2-bromothiazole (2.46 g) in pyridine (25 ml) were stirred under reflux for 20 hours. The reaction mixture was cooled, evaporated and partitioned between chloroform and water. The chloroform layer was evaporated and subjected to medium pressure column chromatography on silica (chloroform:methanol 19:1) to give the title compound as an oil. This was converted to 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]thiazole dihydrochloride, m.p. 192.5°-193.5° C. (recrystallised from isopropanol-ethyl acetate).

Workup

  1. temperatureunder reflux for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. custompartitioned between chloroform and water
  5. customThe chloroform layer was evaporated

Sources & evidence

ORD record
ord-ca83755c830b4af299e6ddd314fea7d4
Source dataset
uspto-grants-1990_08
Patent number
US04952589

Reaction notes

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