Delta-Valerolactone → HCID 22116520, compound

HRID 1276599Notes

Reaction equation

[C:1]1(=O)[O:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]([CH2:11][NH3+:12])[CH2:9][NH3+:10]>>[OH:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]1[NH:12][CH2:11][CH2:8][CH2:9][N:10]=1

Participants

Reactant 2

HCID 10953Delta-Valerolactone

HCID 4030255HCID 4030255, compound

Product 1

HCID 22116520HCID 22116520, compoundYield 49%

Procedure

Using a method similar to Example 1, valerolactone was reacted with 1,3-DAP. At a temperature of 170° C. in the liquid in the flask, 48% of the open-chain amide and 49% of 2-(4-hydroxybutyl)-1,3-diazacyclohex-1-ene were obtained after 8 hours. After a further 8 hours at 180° C. and 8 hours at a liquid-phase temperature of 190° C., the ratio shifted further to 5% of amide and 92% of 2-(4-hydroxybutyl)-1,3-diazacyclohex-1-ene. The subsequent product diazabicyclodecene was obtained in an amount of only 1 or 3%.

Sources & evidence

ORD record: ord-5c51ca19bfe2489f9d2d8fa3e6c17e5b
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166207

Reaction notes

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