Triethylamine → (S)-6-(3-Methylpiperazin-1-yl)nicotinonitrile

HRID 42173Notes

Reaction equation

HRID 42173 reaction equation
C(N(CC)CC)C.Cl[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=1.[CH3:17][C@H:18]1[CH2:23][NH:22][CH2:21][CH2:20][NH:19]1.Cl.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O.O>[CH3:17][C@@H:18]1[NH:19][CH2:20][CH2:21][N:22]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=2)[CH2:23]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 27342192-Methylpiperazine, (S)-HCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 44186249(S)-6-(3-Methylpiperazin-1-yl)nicotinonitrileYield 69.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (4.13 g, 3 mL, 40.8 mmol, 4 eq) is added to a solution of 6-chloro-nicotinonitrile (1.38 g, 10 mmol, 1 eq), (S)-2-methyl-piperazine (1.00 g, 10 mmol, 1 eq) in DMF (15 mL), and the resulting solution is stirred at rt for 14 h. A white precipitate of triethylamine hydrochloride forms in the course of the reaction. Water (15 mL) and EtOAc (100 mL) are added, the organic layer is separated, dried over sodium sulfate and concentrated under reduced pressure to a white residue. The solid is further dried under high vacuum to yield the desired product as a white solid (1.4 g, 69%).

Workup

  1. customthe organic layer is separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure to a white residue
  4. customThe solid is further dried under high vacuum

Sources & evidence

ORD record
ord-7373e526e63343878cd0b20258e7f221
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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