1-Bromoheptane → Eptastigmine

HRID 725207Notes

Reaction equation

HRID 725207 reaction equation
[CH3:1][C@:2]12[C:9]3[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][C:8]=3[N:7]([CH3:15])[C@H:6]1[N:5]([CH3:16])[CH2:4][CH2:3]2.[O-:17][C:18]#[N:19].[K+].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>[Br-].C([N+](CC)(CC)CC)C.C(#N)C>[CH3:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:19][C:18]([O:14][C:11]1[CH:12]=[CH:13][C:8]2[N:7]([CH3:15])[C@H:6]3[N:5]([CH3:16])[CH2:4][CH2:3][C@@:2]3([CH3:1])[C:9]=2[CH:10]=1)=[O:17]

Participants

6

Reactant 3

HCID 123691-BromoheptaneHCID 119198EserolineHCID 11378442Potassium cyanate

Product 1

HCID 65872EptastigmineYield 63%

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

150 g of eseroline (0.69 mole), 83.9 g of potassium cyanate (1.035 moles), 148 g of 1-bromoheptane (0.83 mole) and 29 g of tetraethylammonium bromide (0.14 mole) are placed into 5 l of anhydrous acetonitrile. The reaction mixture is refluxed for 19 hours, the insolubles are filtered off and the mixture is worked up as described in Example 1. Heptastigmine yield is 63%.

Workup

  1. temperatureThe reaction mixture is refluxed for 19 hours
  2. filtrationthe insolubles are filtered off

Sources & evidence

ORD record
ord-6c619a3576e14e828e081d3f7faa104b
Source dataset
uspto-grants-1998_01
Patent number
US05705657

Reaction notes

Loading…