Sodium Hydroxide → Cyclohexanamine, N-methyl-2-(1-pyrrolidinyl)-, trans-

HRID 978065Notes

Reaction equation

HRID 978065 reaction equation
[CH3:1][N:2]1[CH:8]2[CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7]2.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-].[Na+]>[Cl-].[NH4+].O>[CH3:1][NH:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 12396089HCID 12396089, compound

Product 1

HCID 13377463Cyclohexanamine, N-methyl-2-(1-pyrrolidinyl)-, trans-Yield 52.2%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 962WaterSolvent

Procedure

7-Methyl-7-azabicyclo[4.1.0]heptane (7.0 g, 0.063 mol) from the previous step, 17.92 g (0.25 mol) of pyrrolidine, 0.16 g of ammonium chloride, and 10 ml of water were stirred and heated under reflux for 21 hours. The solution was then cooled and solid sodium hydroxide was added and the mixture was extracted three times with 50-ml portions of ether. The combined extracts were dried over anhydrous magnesium sulfate and evaporated under reduced pressure to yield a residual brown oil. This residue was distilled under high vacuum to yield 6.0 g of colorless trans-N-methyl-2-(1-pyrrolidinyl)cyclohexanamine, bp 95° C. (high vacuum).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 21 hours
  3. temperatureThe solution was then cooled
  4. extractionthe mixture was extracted three times with 50-ml portions of ether
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto yield a residual brown oil
  8. distillationThis residue was distilled under high vacuum

Sources & evidence

ORD record
ord-78d403da67414cad94ab4b3650f2a0ea
Source dataset
uspto-grants-1987_05
Patent number
US04663343

Reaction notes

Loading…