Dichloromethane → N-((1-(2-pivalamidoethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

HRID 388773Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)[CH2:6][CH2:5]1.C(Cl)Cl.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].C([O-])(O)=O.[Na+]>CCOC(C)=O.CN(C=O)C>[C:31]([NH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:14]=2)[CH2:8][CH2:9]1)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of N-((1-(2-aminoethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide (70 mg, 0.18 mmol) and TEA (123 μL, 0.881 mmol) in a 1:1 mixture of CH2Cl2:DMF (2 mL) was treated with pivaloyl chloride (42 mg, 0.35 mmol). The reaction mixture was stirred overnight then transferred to a test tube containing saturated aqueous NaHCO3 (4 mL) and EtOAc (4 mL). The biphasic mixture was mixed vigorously and allowed to separate for 15 min. After separation, the mixture was cooled to −20° C. until the aqueous layer was frozen. The organic layer was then poured off and the solvent was removed under reduced pressure at 50° C. The resulting residue was purified by HiTOPs.

Workup

customthen transferred to a test tube
additionThe biphasic mixture was mixed vigorously
customto separate for 15 min
customAfter separation
temperaturewas frozen
additionThe organic layer was then poured off
customthe solvent was removed under reduced pressure at 50° C
customThe resulting residue was purified by HiTOPs

Sources & evidence

ORD record: ord-7457f101120747908dfc814ae09a7cd3
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377968B2

Reaction notes

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