Triethylamine → 1-(5-Coumaranyl carbonyl)-4-(2-thiazolyl) piperazine

HRID 267731Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(N(CC)CC)C.[O:19]1[C:27]2[C:22](=[CH:23][C:24]([C:28](Cl)=[O:29])=[CH:25][CH:26]=2)[CH2:21][CH2:20]1>O1CCCC1>[O:19]1[C:27]2[C:22](=[CH:23][C:24]([C:28]([N:9]3[CH2:8][CH2:7][N:6]([C:2]4[S:1][CH:5]=[CH:4][N:3]=4)[CH2:11][CH2:10]3)=[O:29])=[CH:25][CH:26]=2)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 9 g of 1-(2-thiazolyl) piperazine and 5 g of anhydrous triethylamine in 200 ml of anhydrous tetrahydroduran, there were added dropwise, a solution of 9.1 g of 5-coumaranyl carboxylic acid chloride in 20 ml of tetrahydrofuran. After the completion of the addition, the reaction mixture was heated at 60° C for two hours, then, the so-formed precipitate was suction-filtered off. The filtrate was evaporated under reduced pressure and the crystalline residue was washed with water then recrystallized in 70 ml of ethanol. There were obtained 12 g of 1-(5-coumaranyl carbonyl)-4-(2-thiazolyl) piperazine, melting (K) at 150°-151° C.

Workup

additionAfter the completion of the addition
filtrationthe so-formed precipitate was suction-filtered off
customThe filtrate was evaporated under reduced pressure
washthe crystalline residue was washed with water
customthen recrystallized in 70 ml of ethanol

Sources & evidence

ORD record: ord-b763e8445bf2457c9c8413ea56394967
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03944551

Reaction notes

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