Methylamine → 1-Cyclohexyl-N-methylpyrrolidin-3-amine

HRID 1031177Notes

Reaction equation

HRID 1031177 reaction equation
[CH3:1][NH2:2].Br[CH:4]1[CH2:8][CH2:7][N:6]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:5]1>C(O)C>[CH:9]1([N:6]2[CH2:7][CH2:8][CH:4]([NH:2][CH3:1])[CH2:5]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 198197303-Bromo-1-cyclohexylpyrrolidine

Product 1

HCID 128957171-Cyclohexyl-N-methylpyrrolidin-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 40% aqueous methylamine (93 g), ethanol (200 ml) and 3-bromo-1-cyclohexylpyrrolidine (92.8 g, 0.4 mol) was heated to 150° C. in a steel bomb for 20 hr. After cooling, the mixture was concentrated and the residue partitioned between dilute sodium hydroxide and chloroform. The chloroform solution was dried (sodium sulfate), concentrated, and the residue distilled to obtain 40 g (55%), bp 172°-176° C./40 mm. A portion of the distillate was converted to the fumarate salt which was recrystallized from ethanol-water. This was converted back to the free base and distilled, bp 75°-80° C./0.1 mm.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. customthe residue partitioned between dilute sodium hydroxide and chloroform
  4. dry with materialThe chloroform solution was dried (sodium sulfate)
  5. concentrationconcentrated
  6. distillationthe residue distilled
  7. customto obtain 40 g (55%), bp 172°-176° C./40 mm
  8. customwas recrystallized from ethanol-water
  9. distillationdistilled

Sources & evidence

ORD record
ord-b6a0d3563d624d68a285c2bd4fb30d40
Source dataset
uspto-grants-1992_04
Patent number
US05109013

Reaction notes

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