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Hydrochloric Acid → Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMate

HRID 340420
Notes
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Reaction equation

HRID 340420 reaction equation
[CH3:1][O-:2].[Na+].Br[N:5]1[C:9](=[O:10])CCC1=O.[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[C:22](C(N)=O)=[CH:21][N:20]=2)[CH2:15][CH2:14]1.Cl>CO.ClCCl>[CH3:1][O:2][C:9](=[O:10])[NH:5][C:22]1[CH:21]=[N:20][C:19]([N:16]2[CH2:15][CH2:14][N:13]([CH3:12])[CH2:18][CH2:17]2)=[CH:27][C:26]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 114837284-(2-Methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinecarboxamide

Product 1

HCID 12167320Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMateYield 102.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×
HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

2.15 ml (11.6 mMol) Sodium methoxide in methanol were added over 30 minutes to a suspension of 0.85 g (4.6 mMol) N-bromosuccinimide in 5.0 ml dichloromethane cooled to −5° C. The reaction mixture was stirred 16 hours at −5° C. Still at this temperature, a solution of 1.0 g (3.1 mMol) 6-(4-methyl-piperazin-1-yl)-4-o-tolyl-nicotinamide in 5.0 ml methanol was added over 20 minutes and stirred for 5 hours. 7.1 ml (7.1 mMol) Aqueous HCl 1N and 20 ml dichloromethane were added. The phases were separated and the organic phase was washed with deionized water. The aqueous phases were extracted with dichloromethane, brought to pH=8 with aqueous NaOH 1N and further extracted with dichloromethane. The latter organic, extracts were combined, dried (Na2SO4) and concentrated to yield 1.08 g (quant.) [6-(4-methyl-piperazin-1yl)-4-o-tolyl-pyridin-3-yl]-carbamic acid methyl ester as a grey foam. MS (ISP): 341 (M+H+, 100), 284 (35).

Workup

  1. stirringstirred for 5 hours
  2. customThe phases were separated
  3. washthe organic phase was washed with deionized water
  4. extractionThe aqueous phases were extracted with dichloromethane
  5. extractionfurther extracted with dichloromethane
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dfd27b17e5dd4bd89f95215e61192b2e
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895586B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes