1-Methylpiperazine → HCID 131715415, compound

HRID 986090Notes

Reaction equation

C(C[CH:5]1[C:13](=O)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:11]=2)[N:6]1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)(O)=O.[Mg+2].[Cl-:27].[Cl-].[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>CN(P(N(C)C)(N(C)C)=O)C>[ClH:27].[ClH:27].[F:25][C:22]1[CH:23]=[CH:24][C:19]([N:6]2[C:7]3[C:12](=[CH:11][C:10]([C:15]([F:18])([F:16])[F:17])=[CH:9][CH:8]=3)[C:13]([NH+:33]3[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]3)=[CH:5]2)=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 200 °C

Procedure

2-Carboxymethyl-1-(4'-fluorophenyl)-5-trifluoromethylindolin-3-on (15 g) and MgCl2. 6H2O (30 g) in HMPA (100 ml) were heated under N2 at 120°-140° C. for 1 h and finally at 150° C. for another 1/2 h. 1-Methylpiperazin (25 ml) was added and the mixture was refluxed under N2 at an oil bath temperature of 200° C. for 16 h. The mixture was cooled and poured into 1 ltr. of H2O and extracted with ether (3×200 ml). The combined ether extracts were washed with 0.5 M HCl (3×300 ml). The acidic H2O phase was made alkaline and reextracted with ether (2×200 ml). The combined organic phase was dried (MgSO4) and the ether evaporated. The remaining oil was dissolved in acetone and the title compound precipitated as a dihydrochloride. Yield: 6.7 g (35%). M.p. 245°- 247° C.

Workup

temperatureThe mixture was cooled
additionpoured into 1 ltr
extractionof H2O and extracted with ether (3×200 ml)
washThe combined ether extracts were washed with 0.5 M HCl (3×300 ml)
dry with materialThe combined organic phase was dried (MgSO4)
customthe ether evaporated
dissolutionThe remaining oil was dissolved in acetone
customthe title compound precipitated as a dihydrochloride

Sources & evidence

ORD record: ord-a076db4a71194c9c9b3e0dc5d2500435
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04710500

Reaction notes

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