Dioxocyclam → 1,4,8,11-Tetraazacyclotetradecane

HRID 2394800Notes

Reaction equation

HRID 2394800 reaction equation
[CH2:1]1[CH2:16][NH:15][CH2:14][CH2:13][NH:12][C:10](=O)[CH2:9][C:7](=O)[NH:6][CH2:5][CH2:4][NH:3][CH2:2]1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>>[NH:3]1[CH2:2][CH2:1][CH2:16][NH:15][CH2:14][CH2:13][NH:12][CH2:10][CH2:9][CH2:7][NH:6][CH2:5][CH2:4]1

Participants

3

Reactant 2

HCID 196413DioxocyclamHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 649641,4,8,11-Tetraazacyclotetradecane

Procedure

bisacylating 1,3-diaminopropane by reacting it with 2 equivalents of chloroacetyl chloride in the presence of an alkali metal carbonate and a chlorinated aliphatic hydrocarbon at a temperature of from 0° to 30° C. for a period of between 90 minutes and 4 hours to obtain the dichlorodiamide compound of formula I ##STR5## 2) cyclizing the dichlorodiamide compound prepared in the first step by reacting it with an quivalent amount of 1,3-diaminopropane in the presence of an alkali metal carbonate and acetonitrile at a temperature of from 78° to 83° C. for a period of between 20 and 30 hours to obtain dioxocyclam of formula II ##STR6## 3) reducing the dioxocyclam compound prepared in the second step by reacting it with sodium bis(2-methoxy-ethoxy) aluminum hydride in the presence of an aromatic hydrocarbon at a temperature of from 20° to 35° C. for a period of between 90 minutes and 4 hours to obtain 1,4,8,11-tetraazacyclotetradecane of formula III ##STR7##

Workup

  1. customprepared in the second step
  2. customof from 20° to 35° C.
  3. customof between 90 minutes and 4 hours

Sources & evidence

ORD record
ord-c2b27faaaa064ec3972a2cf7bec8ac0c
Source dataset
uspto-grants-1998_09
Patent number
US05811544

Reaction notes

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