Dimethylformamide → 2-[4-(4-Indolyl)-1-piperazinyl]-N-(2-pyridyl)acetamide

HRID 1603684Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[C:5]([N:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CO[CH:18](OC)[CH2:19][NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(N(C(C)C)CC)(C)C.CN(C)C=[O:41]>O>[NH:1]1[C:9]2[C:4](=[C:5]([N:10]3[CH2:15][CH2:14][N:13]([CH2:18][C:19]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)=[O:41])[CH2:12][CH2:11]3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1.4 g of 1-(4-indolyl)piperazine, 1.26 g of 2-chloro-N-(2-pyridyl)acetamide (prepared as described in Beilstein E III/IV, 22, 3881), 1.3 ml of diisopropylethylamine, and 14 ml of N,N-dimethylformamide was stirred at 60° C. under nitrogen stream for 4 h. Afterwards, the mixture was diluted with 200 ml of water and extracted with ethyl acetate (4×50 ml). The organic layers were washed with water, dried (sodium sulfate) and evaporated to dryness in vacuo affording 2.37 g of the title compound as a crude base, which was crystallized from MeOH affording 1.6 g melting at 198-201° C.

Workup

extractionextracted with ethyl acetate (4×50 ml)
washThe organic layers were washed with water
dry with materialdried (sodium sulfate)
customevaporated to dryness in vacuo

Sources & evidence

ORD record: ord-a757ef06a9c641ab98a51fe405922aa3
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990114

Reaction notes

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