N,N'-Bis(2-aminoethyl)-1,3-propanediamine → 4-(5,7-Dioxo-1,4,8,11-tetraazacyclotetradecan-6-yl)butanenitrile

HRID 46641Notes

Reaction equation

HRID 46641 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH:6]1[C:18](=[O:19])[NH:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9][NH:8][C:7]1=[O:20])#[N:2].N[CH2:22]CNCCCNCCN>>[C:1]([CH2:3][CH2:4][CH2:5][CH:6]1[C:7](=[O:20])[NH:8][CH2:9][CH2:10][NH:11][CH2:22][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][NH:17][C:18]1=[O:19])#[N:2]

Participants

3

Reactant 2

HCID 78479N,N'-Bis(2-aminoethyl)-1,3-propanediamineHCID 203867633-(3-Cyanopropyl)-2,4-dioxo-1,5,8,11-tetraazacyclotridecane

Product 1

HCID 123652014-(5,7-Dioxo-1,4,8,11-tetraazacyclotetradecan-6-yl)butanenitrileYield 30%

Procedure

The procedure of (2) of Example 1 was repeated with the exception that N,N'-bis(2-aminoethyl)-1,3-propylenediamine was used in place of triethylenetetramine. Thus, 3-(3-cyanopropyl)-2,4-dioxo-1,5,8,12-tetraaza-cyclotetradecane (C-substituted cyclic diamide) was obtained in a yield of 30%.

Sources & evidence

ORD record
ord-550cf5d5cb87479f92c09e9963b1db77
Source dataset
uspto-grants-1979_11
Patent number
US04174428

Reaction notes

Loading…