Methane → 3-(2,2-Dimethylpropylideneamino)-pyrrolidine

HRID 346318

Reaction equation

HRID 346318 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][C:15]2[CH:20]=CC=C[CH:16]=2)[CH2:9]1)C1C=CC=CC=1.[CH4:21]>CO.[Pd]>[CH3:21][C:15]([CH3:16])([CH3:20])[CH:14]=[N:13][CH:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 297MethaneHCID 14098325N,N'-Dibenzyl-3-aminopyrrolidine

Product 1

HCID 148366043-(2,2-Dimethylpropylideneamino)-pyrrolidineYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

36.8 g (0.138 mol) of 1-benzyl-3-benzylaminopyrrolidine are hydrogenated in 160 ml of methanol over 5 g of 5% strength palladium on active charcoal at 130° C. under a hydrogen pressure of 100 bar for 10 hours. The catalyst is filtered off and 16.6 g (0.138 mol) of 71% strength pivalaldehyde are added to the filtrate, while stirring, after which the temperature rises from 20° C. to 28° C. The mixture is subsequently stirred for 30 minutes, the methanol is removed on a rotary evaporator and the residue is distilled. 12.7 g of 3-(2,2-dimethyl-propylidene-amino)-pyrrolidine of boiling point: 61° C./10 mbar are obtained with a purity, determined by gas chromatography, of 97%, corresponding to a yield of 58% of theory.

Workup

  1. customfor 10 hours
  2. filtrationThe catalyst is filtered off
  3. addition16.6 g (0.138 mol) of 71% strength pivalaldehyde are added to the filtrate
  4. customrises from 20° C. to 28° C
  5. stirringThe mixture is subsequently stirred for 30 minutes
  6. customthe methanol is removed on a rotary evaporator
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-397b27d5e4434114aa4ca9609b44ebb5
Source dataset
uspto-grants-1991_10
Patent number
US05061712

Linked notes

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