Ethanol → HCID 67821818, compound

HRID 1707881Notes

Reaction equation

Cl[C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][C@H:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:10])=[O:7])=[CH:4][N:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[CH2:24]([OH:26])[CH3:25]>O>[N:18]1([C:2]2[CH:17]=[CH:16][C:25]([C:24]([O:8][C@H:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:10])=[O:26])=[CH:4][N:3]=2)[CH2:23][CH2:22][N:21]([C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][C@H:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:10])=[O:7])=[CH:4][N:3]=2)[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1.4 g of (S)-1-(ethoxycarbonyl)ethyl 6-chloronicotinate, 0.2 g of piperazine and 25 ml of ethanol was heated at 80° C. for 2 days. The reaction mixture was treated with 500 ml of water and then extracted three times with 100 ml of diethyl ether each time. The combined organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time, dried over magnesium sulphate, filtered and subsequently concentrated. The residue was chromatographed on silica gel with toluene/ethyl acetate (vol. 4:1). Recrystallization from ethanol gave pure bis-[(S)-1-(ethoxycarbonyl)ethyl] 6,6'-(1,4-piperazinediyl)dinicotinate with m.p. (C-I) 143° C., [α]20 589 =+68.3 °.

Workup

extractionextracted three times with 100 ml of diethyl ether each time
washThe combined organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationsubsequently concentrated
customThe residue was chromatographed on silica gel with toluene/ethyl acetate (vol. 4:1)
customRecrystallization from ethanol

Sources & evidence

ORD record: ord-7425f6f2ba2742c28e2783df10a0206b
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05356559

Reaction notes

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