Benzoic Acid → 4-Isopropylamino-1-(4-methoxypyrid-3-ylmethyl)piperidine monobenzoic acid salt

HRID 1181514Notes

Reaction equation

[CH:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[O:18][CH3:19])[CH2:7][CH2:6]1)([CH3:3])[CH3:2].[C:20]([OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(OC)(C)C>[C:20]([OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH:1]([NH:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[O:18][CH3:19])[CH2:9][CH2:10]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 52.5 °C

Procedure

To a 1L reaction flask equipped with a mechanical stirrer and a nitrogen inlet was added 4-isopropylamino-1-(4-methoxypyrid-3-ylmethyl)piperidine (45.7 g, 0.174 mol) and 200 mL of MTBE. The resulting mixture was heated to 50-55° C. to dissolve the solid. To this solution was added a solution of benzoic acid (21.3 g, 0.174 mol) in 100 mL of MTBE at 50-55° C. (Note: Heat may be needed to dissolve the benzoic acid in MTBE). This mixture was stirred at 50-55° C. for 30 minutes and then stirred at room temperature for 16 hours. The resulting solid was filtered and washed with 50 mL of MTBE and then dried under vacuum at 40° C. for 16 hours to give 54.9 g of the title intermediate as a white solid (82% yield; ≧99% purity).

Workup

customequipped with a mechanical stirrer and a nitrogen inlet
dissolutionto dissolve the solid
temperatureHeat may
stirringstirred at room temperature for 16 hours
filtrationThe resulting solid was filtered
washwashed with 50 mL of MTBE
customdried under vacuum at 40° C. for 16 hours

Sources & evidence

ORD record: ord-a87c5e90bd2a4943ac0f24fbc8b26e85
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285564B2

Reaction notes

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