4-Methylbenzoyl Chloride → HCID 59294619, compound

HRID 2195609Notes

Reaction equation

[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH2:14])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.[OH-].[Na+]>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:22](=[O:23])[C:21]3[CH:25]=[CH:26][C:18]([CH3:17])=[CH:19][CH:20]=3)[CH2:9]2)=[O:7])=[CH:15][CH:16]=1

Participants

Reactant 3

HCID 134054-Methylbenzoyl Chloride

HCID 14798Sodium Hydroxide

HCID 28875263HCID 28875263, compound

Product 1

HCID 59294619HCID 59294619, compoundYield 80.4%

Conditions

Temperature: 15 °C

Procedure

To the aqueous solution of (R)-1-(p-methylbenzoyl)-3-amino piperidine obtained in Example 13 (amount: 3 g), p-Methylbenzoyl chloride (0.16 g) was added. The pH of the mixture was kept from 8.0 to 9.0 using sodium hydroxide. The mixture was stirred at 15° C. for 3 hours, and the precipitated crystal was filtered off. The crystal was dried under reduced pressure to obtain the title compound as white crystal (0.28 g, yield: 59%).

Workup

filtrationthe precipitated crystal was filtered off
customThe crystal was dried under reduced pressure

Sources & evidence

ORD record: ord-5c33df73789544ab8dd1231010be1011
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338142B2

Reaction notes

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