Formaldehyde → HCID 66936371, compound

HRID 1366451Notes

Reaction equation

HRID 1366451 reaction equation
[CH3:1][C@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[CH2:15]=O>C(Cl)Cl>[CH3:1][C@H:2]1[N:7]([CH3:15])[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 2756811(R)-1-Boc-3-methylpiperazine

Product 1

HCID 66936371HCID 66936371, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercially available 1,1-dimethylethyl (3R)-3-methyl-1-piperazinecarboxylate (2.78 g, 13.88 mmol), formaldehyde (37% in water) (1.94 mL), sodium triacetoxy borohoydride (5.03 g, 23.73 mmol) and DCM (200 mL) were stirred overnight. The solvent was removed, and 1N NaOH was added to the residue. The mixture was extracted with dichloromethane, and the organics were dried (Na2SO4) and concentrated in vacuo to provide 1,1-dimethylethyl (3R)-3,4-dimethyl-1-piperazinecarboxylate as a clear oil (2.70 g, 91%). LCMS: (M+H)+=215.4.

Workup

  1. customThe solvent was removed
  2. addition1N NaOH was added to the residue
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialthe organics were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8fdacaafc6341a88e754d89be38435e
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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