Triethylamine → Ethyl 4-{2-[1-(2-phenoxypropyl)-piperazin-4-yl]-ethyl}-benzoate

HRID 2290456Notes

Reaction equation

HRID 2290456 reaction equation
[O:1]([CH:8]([CH3:16])[CH2:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1.C(N(CC)CC)C>O1CCCC1>[O:1]([CH:8]([CH3:16])[CH2:9][N:10]1[CH2:11][CH2:12][N:13]([CH2:18][CH2:19][C:20]2[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=2)[CH2:14][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12748305Ethyl 4-(2-bromoethyl)benzoateHCID 202327071-(2-Phenoxypropyl)-piperazine

Product 1

HCID 20232445Ethyl 4-{2-[1-(2-phenoxypropyl)-piperazin-4-yl]-ethyl}-benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8.2 g. (37 mmole) 1-(2-phenoxypropyl)-piperazine, 9.57 g. (37 mmole) ethyl 4-(2-bromoethyl)-benzoate, 3.77 g. (37 mmole) triethylamine and 100 ml. anhydrous tetrahydrofuran is heated for 36 hours at reflux temperature and then evaporated. The residue is taken up in diethyl ether and the hydrochloride precipitated from this solution with hydrogen chloride-containing diethyl ether to give 14.7 g. (84% of theory) of the desired compound as a hydrochloride; m.p. 232° C.

Workup

  1. additionA mixture of 8.2 g
  2. temperatureat reflux temperature
  3. customevaporated
  4. customthe hydrochloride precipitated from this solution with hydrogen chloride-
  5. additioncontaining diethyl ether
  6. customto give 14.7 g

Sources & evidence

ORD record
ord-b8b89a2261394329bacb0a55abf36c16
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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