Water → N-((2-(4-(4-Chlorophenoxy)piperidine-1-carbonyl)pyridin-4-yl)methyl)pivalamide

HRID 2170856Notes

Reaction equation

HRID 2170856 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:20]=[C:19]([CH2:21][NH:22][C:23](=O)[O:24]C(C)(C)C)[CH:18]=[CH:17][N:16]=3)=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:41](Cl)(=O)[C:42](C)([CH3:44])[CH3:43].O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:20]=[C:19]([CH2:21][NH:22][C:23](=[O:24])[C:42]([CH3:44])([CH3:43])[CH3:41])[CH:18]=[CH:17][N:16]=3)=[O:14])[CH2:9][CH2:8]2)=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 68204542HCID 68204542, compound

Product 1

HCID 67168082N-((2-(4-(4-Chlorophenoxy)piperidine-1-carbonyl)pyridin-4-yl)methyl)pivalamideYield 45.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-(aminomethyl)pyridin-2-yl)(4-(4-chlorophenoxy)piperidin-1-yl)methanone (25 mg, 0.072 mmol. Example 321), N,N-diisopropylethylamine (0.038 mL, 0.22 mmol) in dichloromethane (1 mL) was added pivaloyl chloride (0.011 mL, 0.087 mmol) at room temperature. After stirring at room temperature for 2 hours, the mixture was poured into water (3 mL). This was extracted with ethyl acetate (4 mL) and washed with water (3 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate) and then preparative LC-MS to give 14.0 mg (45% yield) of the title compound.

Workup

  1. extractionThis was extracted with ethyl acetate (4 mL)
  2. washwashed with water (3 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography (NH-gel, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-bdb962e4f92f496f87cc198e521e3ff4
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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