Butylamine → Trans-4-n-butylamino-1-ethyl-3-pyrrolidinol

HRID 126928Notes

Reaction equation

HRID 126928 reaction equation
[O:1]1[CH:6]2[CH:2]1[CH2:3][N:4]([CH2:7][CH3:8])[CH2:5]2.[CH2:9]([NH2:13])[CH2:10][CH2:11][CH3:12]>Cl>[CH2:9]([NH:13][C@@H:2]1[CH2:3][N:4]([CH2:7][CH3:8])[CH2:5][C@H:6]1[OH:1])[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 13320194N-ethyl-3,4-epoxypyrrolidine

Product 1

HCID 70563799Trans-4-n-butylamino-1-ethyl-3-pyrrolidinol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Conditions

Temperature
150 °C

Procedure

A mixture of 22.6 g (0.20 mole) of 3,4-epoxy-1-ethyl-pyrrolidine, 29.2 g (0.40 mol) of n-butylamine and one drop of conc. hydrochloric acid was heated in a bomb at 150° C. for 20 hr. The mixture was cooled to room temperature, diluted with 350 ml of petroleum ether, cooled in an ice bath and the precipitate was collected. The yield of pure compound as white flakes in this step was 18.0 g (48%); m.p. 57.5°-59.0° C. The filtrate was concentrated under high vaccum leaving a residue of 17.5 g (47%) of quite pure product. Total yield in the two steps was 35.5 g (about 95%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. temperaturecooled in an ice bath
  3. customthe precipitate was collected
  4. concentrationThe filtrate was concentrated under high vaccum
  5. customleaving a residue of 17.5 g (47%) of quite pure product
  6. customTotal yield in the two steps

Sources & evidence

ORD record
ord-fcd5792b438d476594c4442b5cab0aba
Source dataset
uspto-grants-1981_03
Patent number
US04254135

Reaction notes

Loading…