Triethylamine → 4-(1-((2-Chloropyridin-3-yl)carbonyl)-4-hydroxypiperidin-4-yl)benzonitrile

HRID 240398Notes

Reaction equation

HRID 240398 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.C([C:14]1[CH:27]=[CH:26][C:17]([CH2:18][C:19]2([OH:25])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=C[CH:15]=1)#N.[CH3:28][N:29](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([C:4]([N:22]2[CH2:21][CH2:20][C:19]([C:18]3[CH:15]=[CH:14][C:27]([C:28]#[N:29])=[CH:26][CH:17]=3)([OH:25])[CH2:24][CH2:23]2)=[O:6])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 762582-Chloronicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866808464-(4-Cyanobenzyl)-4-hydroxypiperidine hydrochloride

Product 1

HCID 866808604-(1-((2-Chloropyridin-3-yl)carbonyl)-4-hydroxypiperidin-4-yl)benzonitrileYield 104%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-chloronicotinic acid (0.20 g), 4-(4-cyanobenzyl)-4-hydroxypiperidine hydrochloride (0.32 g), HATU (0.72 g) and triethylamine (0.89 mL) in DMF (4.0 mL) was stirred overnight at room temperature. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and filtered through basic silica gel. The filtrate was concentrated under reduced pressure to give the title compound (0.45 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through basic silica gel
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4484988e028b443190f67489053685ea
Source dataset
uspto-grants-2014_02
Patent number
US08648079B2

Reaction notes

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