1-Piperazinecarboxylic acid, ethyl ester → Ethyl 4-[2-(4-fluorophenyl)ethyl]piperazine-1-carboxylate

HRID 1389278Notes

Reaction equation

HRID 1389278 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20]Br)=[CH:15][CH:14]=1>O>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([CH2:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 5731534-Fluorophenethyl bromide

Product 1

HCID 12679858Ethyl 4-[2-(4-fluorophenyl)ethyl]piperazine-1-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 80 g 1-(ethoxycarbonyl)piperazine and 41 g of 2-(4-fluorophenyl)ethyl bromide is kept at room temperature overnight and then heated to 100° C. for 1 hour. After cooling, it is diluted with 50 ml water and extracted with benzene. The extract is washed with water and then shaken with 5% hydrochloric acid. The separated solid hydrochloride is filtered off, washed with a small quantity of water, decomposed by treatment with aqueous ammonia and the base isolated again by extraction with benzene. Processing of the extract affords 51 g (91%) of the crude 1-(ethoxycarbonyl)-4-(2-[4-fluorophenyl]ethyl)piperazine, b.p. 198° C./3 Torr.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with benzene
  3. washThe extract is washed with water
  4. filtrationThe separated solid hydrochloride is filtered off
  5. washwashed with a small quantity of water
  6. customthe base isolated again by extraction with benzene

Sources & evidence

ORD record
ord-c7a1a6380ce448c7853ba59a71e45744
Source dataset
uspto-grants-1981_01
Patent number
US04243805

Reaction notes

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