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Triethylamine → 1-(6-Chloropyridine-3-carbonyl)-4-methylpiperazine

HRID 68444
Notes
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Reaction equation

HRID 68444 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[CH3:44][N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:48]2[CH2:49][CH2:50][N:45]([CH3:44])[CH2:46][CH2:47]2)=[O:8])=[CH:9][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 792226-Chloronicotinic acidHCID 2724699PyBOP

Product 1

HCID 9020401-(6-Chloropyridine-3-carbonyl)-4-methylpiperazineYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 6-Chloro-nicotinic acid (3.00 g, 19.0 mmol) in 30 mL dimethylformamide was added (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (10.9 g, 20.9 mmol), 1-methylpiperazine (2.30 g, 22.1 mmol). and triethylamine (2.18 g, 21.5 mmol). After stirring for 18 hours, this was partitioned between ethyl acetate and water. The ethylacetate layer was dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (elution with 3% methanol/dichloromethane) to yield (6-Chloro-pyridin-3-yl)-(4-methyl-piperazin-1-yl)-methanone (2.50 g, 9.33 mmol).

Workup

  1. customthis was partitioned between ethyl acetate and water
  2. dry with materialThe ethylacetate layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (elution with 3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-37df375e372a4d86a062148f65fc1a12
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822457B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes