Hydrochloric Acid → 2-[4-(2-Furoyl)-1-piperazinyl]-1-phenyl-indole 3-carboxylic acid 4-methyl-piperazide

HRID 26209Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:9])[CH2:4][CH2:3]1.N1C=CC=CC=1.[O:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[C:42](Cl)=[O:43].Cl>C(Cl)(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[N:25]2[CH2:26][CH2:27][N:28]([C:42]([C:38]3[O:37][CH:41]=[CH:40][CH:39]=3)=[O:43])[CH2:29][CH2:30]2)=[O:9])[CH2:6][CH2:7]1

Participants

Conditions

Temperature: -20 °C

Procedure

To a mixture of 16.1 g (0.04 mol) of 1-phenyl-2-(1-piperazinyl)-indole 3-carboxylic acid 4-methyl piperazide (Example 7), 5 ml of pyridine and 40 ml of chloroform, that had been cooled to -20° C., a solution of 6.5 g (0.05 mol) of furan-2-yl carboxylic acid chloride in 80 ml of chloroform was added. The mixture was allowed to stand for 4 hours at room temperature, then 200 ml of chloroform were added and the mixture was washed four times with water. The solvent was eliminated in vacuo, the crystallized residue was digested with ether, suction-filtered and washed with ether. Yield: 19 g (95% of the theoretical yield), m.p. 180°-181° C.; the hydrochloride decomposed above 300° C.

Workup

washthe mixture was washed four times with water
filtrationsuction-filtered
washwashed with ether
customYield: 19 g (95% of the theoretical yield), m.p. 180°-181° C.
customdecomposed above 300° C.

Sources & evidence

ORD record: ord-95440212dd254508a8ceee59d310becf
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04148895

Reaction notes

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