Formic Acid → HCID 29920718, compound

HRID 706557Notes

Reaction equation

HRID 706557 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.C=O.[CH:17](O)=O>CO>[CH3:1][C@@H:2]1[N:7]([CH3:17])[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 7023035(S)-1-Boc-3-methylpiperazine

Product 1

HCID 29920718HCID 29920718, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (S)-tert-butyl 3-methylpiperazine-1-carboxylate (50 g, 0.250 mol) in 500 mL of methanol was added formaldehyde (41.6 mL, 0.5 mol, 37% aqueous solution) and formic acid (33 mL, 0.874 mol) and the mixture was heated to 70° C. for 16 hours, then concentrated under reduced pressure. The resulting residue was taken up in EtOAc (500 mL), washed with 10% aqueous potassium carbonate, dried over sodium sulfate and concentrated under reduced pressure to give 54 g (100%) of the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with 10% aqueous potassium carbonate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b0a92a2a8874bb49db7985da4dce49c
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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