Hydrochloric Acid → 3,4,5-Trimethylpiperazine-1-carboxylic acid tert-butyl ester

HRID 1437225Notes

Reaction equation

HRID 1437225 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([CH3:14])[NH:11][CH:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C=O.Cl.[H][H].Cl.[CH2:22](O)C>CO.C(O)C.[C].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([CH3:14])[N:11]([CH3:22])[CH:10]([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 712Formaldehyde2×HCID 21887872Ethanol hydrochlorideHCID 22219990Tert-butyl 3,5-dimethylpiperazine-1-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 670689213,4,5-Trimethylpiperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

3,5-Dimethylpiperazine-1-carboxylic acid tert-butyl ester (3.31 g) obtained from Referential Example 87 was dissolved in methanol (50 mL). To the resultant solution, 10% palladium-carbon (0.504 g), 35% aqueous formalin (1.85 mL), and 1M HCl in ethanol (15.4 mL) were added at room temperature, and the mixture was stirred in a hydrogen atmosphere for 19 hours. 10% Palladium-carbon (0.95 g), 35% aqueous formalin (1.8 mL), and 1M HCl-ethanol (15 mL) were added thereto, followed by stirring in a hydrogen atmosphere for 23 hours. After the system was purged with nitrogen, the resultant mixture was neutralized through addition of the aqueous sodium hydroxide, and insoluble matter was removed by filtration. The filtrate was brought to dryness under reduced pressure. The residue was purified through silica gel column chromatography (chloroform−7N ammonia/methanol), to thereby give the title compound as an oily product (2.28 g, 65%).

Workup

  1. customAfter the system was purged with nitrogen
  2. additionthe resultant mixture was neutralized through addition of the aqueous sodium hydroxide, and insoluble matter
  3. customwas removed by filtration
  4. customThe residue was purified through silica gel column chromatography (chloroform−7N ammonia/methanol)

Sources & evidence

ORD record
ord-459543db04c443588bbe08d5b7416eda
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

Loading…