Diisopropylethylamine → N-((3-chloropyrazin-2-yl)methyl)-1-methylpiperidine-4-carboxamide

HRID 245715Notes

Reaction equation

HRID 245715 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:9]([Cl:10])=[N:8][CH:7]=[CH:6][N:5]=1.C(N(CC)C(C)C)(C)C.Cl.[CH3:21][N:22]1[CH2:27][CH2:26][CH:25]([C:28](Cl)=[O:29])[CH2:24][CH2:23]1>ClCCl>[Cl:10][C:9]1[C:4]([CH2:3][NH:2][C:28]([CH:25]2[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]2)=[O:29])=[N:5][CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 219565061-Methylpiperidine-4-carbonyl chloride hydrochlorideHCID 42614233(3-Chloropyrazin-2-yl)methanamine hydrochloride

Product 1

HCID 86674656N-((3-chloropyrazin-2-yl)methyl)-1-methylpiperidine-4-carboxamideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-aminomethyl-3-chloropyrazine hydrochloride (content 70%; 7.85 mmol, 1.7 g) in N,N-diisopropylethylamine (39.3 mmol, 6.84 ml) and dichloromethane (30 ml) at 0° C. was added carefully 1-methylpiperidine-4-carbonyl chloride hydrochloride (9.42 mmol, 2.2 g). Then the cooling bath was removed. After two hours saturated aqueous sodium hydrogencarbonate solution (40 mL) was added and extracted five times with dichloromethane (30 mL). The organic extracts were combined, dried and concentrated and co-evaporated twice with toluene to give N-((3-chloropyrazin-2-yl)methyl)-1-methylpiperidine-4-carboxamide (1.75 g)

Workup

  1. customThen the cooling bath was removed
  2. additionAfter two hours saturated aqueous sodium hydrogencarbonate solution (40 mL) was added
  3. extractionextracted five times with dichloromethane (30 mL)
  4. customdried
  5. concentrationconcentrated and co-evaporated twice with toluene

Sources & evidence

ORD record
ord-cecd7771d0874393849b42ddf1dda520
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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