Water → HCID 21473427, compound

HRID 2294145Notes

Reaction equation

F[C:2](F)(F)[C:3]([NH:5][C:6]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=O.[H-].[Na+].ClCC[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[O:38][CH3:39])[CH2:28][CH2:27]1.O>CN(C=O)C>[CH3:39][O:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[N:29]1[CH2:28][CH2:27][N:26]([CH2:25][CH2:2][CH2:3][NH:5][C:6]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:7]=2[C:8]([N:10]([CH3:12])[CH3:11])=[O:9])[CH2:31][CH2:30]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-trifluoroacetylamino-N,N,3-trimethylbenzamide (584.2 mg, 2.13 mmol), prepared as in Example 22, and sodium hydride (110 mg, 2.7 mmol) in 10 mL of DMF was heated at 50° C. for 20 minutes and then 1-chloro-3-[4-(2-methoxyphenyl)piperazin-1-yl]propane (647 mg, 2.13 mmol) was added. The mixture was heated at 80° C. for 18 hours, then poured into water and extracted with ethyl acetate (3×50 mL). The combined extract was washed with saline, dried (MgSO4) and concentrated. The residue was purified on silica gel by column chromatography eluting with 6% methanol/methylene chloride to give 2-{3-[4-(2-methoxy-phenyl)piperazin-1-yl]propylamino}-N,N,3-trimethylbenzamide (100 mg, 0.24 mmol).

Workup

temperatureThe mixture was heated at 80° C. for 18 hours
extractionextracted with ethyl acetate (3×50 mL)
extractionThe combined extract
washwas washed with saline
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified on silica gel by column chromatography
washeluting with 6% methanol/methylene chloride

Sources & evidence

ORD record: ord-4d0d5606a754417e84ca6051e9cd738a
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688795

Reaction notes

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