Potassium Carbonate → HCID 66760760, compound

HRID 889177Notes

Reaction equation

HRID 889177 reaction equation
Cl.[CH3:2][NH:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].C([O-])([O-])=O.[K+].[K+].[C:18]([O:22][C:23](=[O:27])[CH:24](Br)[CH3:25])([CH3:21])([CH3:20])[CH3:19]>C(#N)C>[CH3:2][NH:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:25][CH2:24][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:27])[CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 545327tert-Butyl 2-bromopropanoateHCID 11672769479611-85-3

Product 1

HCID 66760760HCID 66760760, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of N-methylpiperazine-1-carboxamide hydrochloride (6 g, 33.52 mmol) and K2CO3 (9.26 g, 67.0 mmol) in acetonitrile (100 mL) was added bromopropionic acid tert-butyl ester (8.4 g, 40.2 mmol). The reaction mixture was stirred at reflux for 12 h, cooled to room temperature and partitioned in ethyl acetate (200 mL) and water (100 mL). Organic layer was separated, dried (MgSO4), and concentrated to give tert-butyl 3-(4-(methylcarbamoyl)piperazin-1-yl)propanoate as an oil which was dissolved in a mixture of dichloromethane (100 mL) and TFA (trifluoroacetic acid) (20 mL) and then stirred overnight. The volatiles were removed under vacuum. The residue was dissolved in methanol, 1N hydrogen chloride in ether was added, and then the solution was concentrated to give 3-(4-(methylcarbamoyl)piperazin-1-yl)propanoic acid as a solid. LCMS 216 (M+1)

Workup

  1. temperatureat reflux for 12 h
  2. custompartitioned in ethyl acetate (200 mL)
  3. customOrganic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-38ba2ed12d1041d6af9b6abb9c2453f6
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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