2-Bromothiazole → HCID 14022497, compound

HRID 2118970Notes

Reaction equation

HRID 2118970 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-0043b269a26c4a928afab7caece0220f
Source dataset
uspto-grants-1987_07
Patent number
US04681883

Reaction notes

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