Diisopropylethylamine → 1-(4-(6-Chloropyridin-3-yl)piperazin-1-yl)-2-(dimethylamino)ethanone

HRID 79185Notes

Reaction equation

HRID 79185 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl.[CH3:15][N:16]([CH2:18][C:19](Cl)=[O:20])[CH3:17].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:19](=[O:20])[CH2:18][N:16]([CH3:17])[CH3:15])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 99643631-(6-Chloropyridin-3-yl)piperazineHCID 139949912-(Dimethylamino)acetyl chloride hydrochloride

Product 1

HCID 582996521-(4-(6-Chloropyridin-3-yl)piperazin-1-yl)-2-(dimethylamino)ethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(6-chloropyridin-3-yl)piperazine (250 mg, 1265 μmol) and dimethylaminoacetyl chloride hydrochloride, 85% (260 mg, 1644 μmol) were dissolved in DMF (6 mL) and DIEA (661 μl, 3794 μmol).). The reaction was stirred at room temperature for 4 hours and then 20 hours at 60° C. The resulting solution was taken up in ethyl acetate 80 mL) and washed with aqueous K2CO3 (10%, 70 mL), water (70 mL), and brine (70 mL). The organic phase was dried (MgSO4) and evaporated to give a brown oil. Silica gel chromatography (gradient elution dichloromethane/0-10% 2M NH3 in methanol) afforded compound 300 as an orange tar (174 mg, 49%).

Workup

  1. custom20 hours
  2. customat 60° C
  3. washwashed with aqueous K2CO3 (10%, 70 mL), water (70 mL), and brine (70 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customto give a brown oil
  7. washSilica gel chromatography (gradient elution dichloromethane/0-10% 2M NH3 in methanol)

Sources & evidence

ORD record
ord-76972208259345499b02ba8f9331a0d9
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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