Amantadine → HCID 19427051, compound

HRID 1033079Notes

Reaction equation

HRID 1033079 reaction equation
[C:1]12([NH2:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:12](OCC)(OCC)(OCC)[CH3:13].[CH:23]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>>[C:1]12([NH:11][C:12](=[N:29][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH3:13])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 3

HCID 2130AmantadineHCID 7965CyclohexylamineHCID 66221Triethyl orthoacetate

Product 1

HCID 19427051HCID 19427051, compoundYield 2.8%

Procedure

Adamantyl amine (1.87 g, 10 mmol), triethyl orthoacetate (1.62 g, 10 mmol) and cyclohexyl amine (0.99 g, 10 mmol) were mixed together then placed in preheated oil bath (140° C.) under nitrogen. After 5 min the reaction became exothermic and the reaction mixture became a slurry and upon continuation for 20 min it became a clear colorless solution. Now the reflux condenser was then replaced by distillation condenser and the low volatiles were distilled off at 75°-77° C. (head temperature) and later the undistilled residue was dried on manifold to give a light-yellow solid. The crude product was flash chromatographed on silica gel using chloroform as eluent to afford the title compound (0.076 g, 2.78%) as a white solid.

Workup

  1. customthen placed in preheated oil bath
  2. custom(140° C.)
  3. waitupon continuation for 20 min it became
  4. distillationNow the reflux condenser was then replaced by distillation condenser
  5. distillationthe low volatiles were distilled off at 75°-77° C. (head temperature)
  6. customlater the undistilled residue was dried on manifold
  7. customto give a light-yellow solid
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-0b577727c2ca4a4ab5322fd7a75b05b3
Source dataset
uspto-grants-1994_05
Patent number
US05308869

Reaction notes

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