Cyclohexylamine → Trans-4-cyclohexylamino-1-ethyl-3-pyrrolidinol

HRID 126929Notes

Reaction equation

HRID 126929 reaction equation
[O:1]1[CH:6]2[CH:2]1[CH2:3][N:4]([CH2:7][CH3:8])[CH2:5]2.[CH:9]1([NH2:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>Cl>[CH:9]1([NH:15][C@@H:2]2[CH2:3][N:4]([CH2:7][CH3:8])[CH2:5][C@H:6]2[OH:1])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 13320194N-ethyl-3,4-epoxypyrrolidine

Product 1

HCID 70563970Trans-4-cyclohexylamino-1-ethyl-3-pyrrolidinolYield 71%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Conditions

Temperature
130 °C

Procedure

A mixture of 11.3 g (0.10 mole) of 3,4-epoxy-1-ethyl-pyrrolidine, 11.9 g (0.12 mol) of cyclohexylamine and one drop of conc. hydrochloric acid was heated at 130° C. under a nitrogen atmosphere for 18 hr. The mixture was cooled and diluted with 200 ml of petroleum ether. The precipitate was collected and recrystallized from petroleum-ether-cyclohexane to give 15 g (71%) of a white powder; m.p. 68°-71° C.

Workup

  1. temperatureThe mixture was cooled
  2. customThe precipitate was collected
  3. customrecrystallized from petroleum-ether-cyclohexane

Sources & evidence

ORD record
ord-573c857830ef45c48c5040f77ac1fb39
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

Loading…