Chloroform → N-{4-[1-(9H-Fluoren-9-yl)-piperidin-4-yl]-butyl)-3-(pyridin-3-yl)-propionamide

HRID 1278963Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:21])[CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:3][CH2:2]1.Br[CH:23]1[C:35]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2.C(Cl)(Cl)Cl.[OH-].[Na+]>C(#N)C>[CH:25]1[C:24]2[CH:23]([N:1]3[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:21])[CH2:13][CH2:14][C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH2:3][CH2:2]3)[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]=2[CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

8.0 g (27.7 mmol) N-(4-piperidin-4-yl-butyl)-3-(pyridin-3-yl)-propionamide and 5.6 g (55.3 mmol) TEA are placed in 100 ml acetonitrile and cooled to ca. 0° C. under moisture exclusion. 6.8 g (27.7 mmol) 9-bromofluorene are added in solid form and the mixture is stirred two days at ca. 65° C. and two days at RT. Subsequently, the solvent is drawn off under vacuum to a large extent, and the residue is dispersed between CHCl3 and 10% NaOH. The organic phase is washed twice with water and dried over sodium sulfate. After the removal of the solvent, the residue is chromatographically purified over silica gel with CHCl3/CH3OH (98/2 to 94/6) and crystallized from 30 ml acetonitrile after drawing off the solvent. Colorless crystals with an MP of 131-132° C.; yield 2.5 g (20%).

Workup

washThe organic phase is washed twice with water
dry with materialdried over sodium sulfate
customAfter the removal of the solvent
customthe residue is chromatographically purified over silica gel with CHCl3/CH3OH (98/2 to 94/6)
customcrystallized from 30 ml acetonitrile

Sources & evidence

ORD record: ord-8000fe15a3c64c1e9b96d6e47d669d9f
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444823B1

Reaction notes

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