Diethyl Ether → HCID 20497515, compound

HRID 2166921Notes

Reaction equation

HRID 2166921 reaction equation
ClC[CH2:3][CH2:4][C:5]#[N:6].[N:7]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11]N[CH2:9][CH2:8]1.C(N(CC)CC)C.CCOCC>C1(C)C=CC=CC=1>[CH2:4]1[CH:5]([N:6]2[CH2:11][CH2:12][N:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8][CH2:9]2)[CH2:3]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 123364-Chlorobutyronitrile

Product 1

HCID 20497515HCID 20497515, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

124 g (1.2 M) of 4-chlorobutyronitrile were dissolved in 600 ml of toluene and the mixture was refluxed under a Dean-Stark separator for 1 hour. The resultant solution was cooled and then 158 g (1 M) of ethyl piperazine-1-carboxylate and 170 ml (1.2 M) of triethylamine were added thereto and the mixture was refluxed for 24 hours. The resulting suspension was cooled to 20° C. and one liter of ether was added thereto. The precipitate of triethylamine hydrochloride was filtered off and the filtrate was decolorized with charcoal and evaporated to dryness to obtain 200 g of ethyl 4-(3-cyclopropyl)-piperazine-1-carboxylate in the form of a brown oil which was distilled under reduced pressure at a boiling point of 140°-150° C. at 0.05 mm Hg.

Workup

  1. temperaturethe mixture was refluxed under a Dean-Stark separator for 1 hour
  2. temperaturethe mixture was refluxed for 24 hours
  3. filtrationThe precipitate of triethylamine hydrochloride was filtered off
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-2d41130d1515457197092fb8c81829f3
Source dataset
uspto-grants-1983_06
Patent number
US04390697

Reaction notes

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