(3-Bromopropyl)benzene → HCID 11989461, compound

HRID 2290458Notes

Reaction equation

HRID 2290458 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(P(N(C)C)(N(C)C)=O)C>[C:24]1([CH2:23][CH2:22][CH2:21][N:4]2[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][C:9]3[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=3)[CH2:2][CH2:3]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 12503(3-Bromopropyl)benzeneHCID 20232457Ethyl 4-[2-(1-piperazinyl)ethyl]benzoate

Product 1

HCID 11989461HCID 11989461, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 40 ml. HMPT, 23.6 g. (90 mmole) ethyl 4-[2-(piperazin-1-yl)-ethyl]-benzoate and 8.96 g. (45 mmole) 3-bromopropylbenzene is maintained at 110° C. for 22 hours, whereby, immediately after mixing together, the temperature increases to about 55° C. and the formation of a pale precipitate is observed. At 110° C., a clear, red-brown solution is present, from which, upon cooling, a product crystallises out. It is poured into a little water, extracted with diethyl ether, the ether phase is washed with water, dried with anhydrous sodium sulphate and evaporated. The crude product is dissolved in diethyl ether and converted into the dihydrochloride by means of hydrogen chloride-containing diethyl ether and recrystallised from ethanol containing 2 drops of concentrated hydrochloric acid; m.p. 273° C. (decomp.). Yield 76% of theory.

Workup

  1. additionA mixture of 40 ml
  2. additionwhereby, immediately after mixing together
  3. customAt 110° C.
  4. temperatureupon cooling
  5. customa product crystallises out
  6. additionIt is poured into a little water
  7. extractionextracted with diethyl ether
  8. washthe ether phase is washed with water
  9. dry with materialdried with anhydrous sodium sulphate
  10. customevaporated
  11. dissolutionThe crude product is dissolved in diethyl ether
  12. additioncontaining diethyl ether
  13. customrecrystallised from ethanol containing 2 drops of concentrated hydrochloric acid

Sources & evidence

ORD record
ord-2d56195009c14de8ac7cb3f36f5c09dc
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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