Pyridine → HCID 66617741, compound

HRID 910464Notes

Reaction equation

HRID 910464 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH3:14])[CH2:9]1)=O)(C)(C)C.N1C=CC=CC=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]1[CH3:14])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 7023035(S)-1-Boc-3-methylpiperazine

Product 1

HCID 66617741HCID 66617741, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

First step: To a stirred solution of commercially available (S)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester (2.38 g, 12 mmol) in CH2Cl2 (25 mL) at 0° C. were added pyridine (1.91 mL, 24 mmol) and methanesulfonyl chloride (0.92 mL, 12 mmol). Stirring was continued at RT overnight, the reaction was poured onto water and extracted with CH2Cl2. The combined organic phases were dried on Na2SO4 and concentrated under vacuo. The crude product was dissolved in CH2Cl2 (20 mL) and TFA (4 mL) was added. After 2 hours at RT, the volatiles were removed under vacuo, the crude was dissolved in CH2Cl2 and washed with aq. NaHCO3 (until pH=8). The organic phase was dried on Na2SO4 and concentrated under vacuo to yield 0.83 g (39%) of (s)-1-methanesulfonyl-2-methyl-piperazine as a light yellow oil.

Workup

  1. additionthe reaction was poured onto water
  2. extractionextracted with CH2Cl2
  3. customThe combined organic phases were dried on Na2SO4
  4. concentrationconcentrated under vacuo
  5. dissolutionThe crude product was dissolved in CH2Cl2 (20 mL)
  6. additionTFA (4 mL) was added
  7. waitAfter 2 hours at RT
  8. customthe volatiles were removed under vacuo
  9. dissolutionthe crude was dissolved in CH2Cl2
  10. washwashed with aq. NaHCO3 (until pH=8)
  11. customThe organic phase was dried on Na2SO4
  12. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-d4b527b8a2094379998b76df4fabc313
Source dataset
uspto-grants-2011_09
Patent number
US08022099B2

Reaction notes

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