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

HRID 267730Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C(N(CC)CC)C.[O:20]1[C:28]2[C:23](=[CH:24][C:25]([C:29](Cl)=[O:30])=[CH:26][CH:27]=2)[CH2:22][CH2:21]1>O1CCCC1>[O:20]1[C:28]2[C:23](=[CH:24][C:25]([C:29]([N:10]3[CH2:11][CH2:12][N:7]([C:2]4[N:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:8][CH2:9]3)=[O:30])=[CH:26][CH:27]=2)[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 8.2 g of 1-(2-pyrimidinyl)-piperazine and 5g of anhydrous triethylamine in 200 ml of anhydrous tetrahydrofuran, 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 2 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-pyrimidinyl) piperazine, melting (K) at 149°-150° 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-f0d9b2d8e54b4adf9aafc3345031bbac
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03944551

Reaction notes

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