Formaldehyde → HCID 19994807, compound

HRID 1110380Notes

Reaction equation

HRID 1110380 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH:5]([CH3:22])[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14]C2C=CC=CC=2)[CH2:10][CH:9]1[CH3:21])=[O:7].C=O.[H][H]>[Pd].CO>[ClH:2].[Cl:2][CH2:3][CH2:4][CH:5]([CH3:22])[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH:9]1[CH3:21])=[O:7]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 19994828HCID 19994828, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19994807HCID 19994807, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 16 parts of 1-(4-chloro-2-methyl-1-oxobutyl)-2-methyl-4-(phenylmethyl)piperazine monohydrochloride, 200 parts of methanol and 7 parts of a formaldehyde solution 40% was hydrogenated at normal pressure and at 60° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the hydrochloride salt in 2-propanol and 2,2'-oxybispropane, yielding 9 parts (72.6%) of 1(-4-chloro-2-methyl-1-oxobutyl)-2,4-dimethylpiperazine monohydrochloride (int. 26).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-9706057aabe14bf3a2f709efe1337d18
Source dataset
uspto-grants-1990_12
Patent number
US04975439

Reaction notes

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