Cyclohexene oxide → HCID 86754875, compound

HRID 1604710Notes

Reaction equation

HRID 1604710 reaction equation
[NH:1]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Li+:13].[Cl-:14].[CH:15]12[O:21][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]2>C(O)(C)C>[OH:21][CH:16]1[CH:17]([N:1]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][N:7]([CH:17]3[CH:16]([OH:21])[CH2:15][CH2:20][CH2:19][CH2:18]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH2:18][CH2:19][CH2:20][CH2:15]1.[Li+:13].[Cl-:14]

Participants

5

Reactant 3

HCID 9246Cyclohexene oxideHCID 649631,4,7,10-TetraazacyclododecaneHCID 433294Lithium Chloride

Product 1

HCID 86754875HCID 86754875, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
0 °C

Procedure

10 g (58.08 mmol) of 1,4,7,10-tetraazacyclododecane, 4.85 g (116.16 mmol) of LiCl and 56.5 g (580.0 mmol) of cyclohexene oxide (7-oxabicyclo[4.1.0]heptane) are suspended in 20 ml of isopropanol and refluxed for 20 hours. Then, the reaction mixture is mixed with 30 ml of isopropanol and slowly cooled to 0° C. The crystals that are obtained are suctioned off, washed with 30 ml of methyl-tert-butyl ether and dried in a vacuum. 19.5 g (82% of theory) of 1,7-bis(6-hydroxycyclohexyl)-1,4,7,10-tetraazacyclododecane LiCl complex is obtained as white crystals. Melting point 170-178° C.

Workup

  1. temperaturerefluxed for 20 hours
  2. customThe crystals that are obtained
  3. washwashed with 30 ml of methyl-tert-butyl ether
  4. customdried in a vacuum
  5. custom19.5 g (82% of theory) of 1,7-bis(6-hydroxycyclohexyl)-1,4,7,10-tetraazacyclododecane LiCl complex is obtained as white crystals

Sources & evidence

ORD record
ord-75a0de9125ad415891ac44f8c1587374
Source dataset
uspto-grants-1999_11
Patent number
US05994536

Reaction notes

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