Piperazine, hexahydrate → 1-(6-Hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-piperazine

HRID 1382208Notes

Reaction equation

HRID 1382208 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][CH2:8][CH:7]2[CH:5]([O:6]2)[CH2:4][O:3]1.O.O.O.O.O.O.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C(#N)C>[OH:6][CH:5]1[CH2:4][O:3][C:2]([CH3:1])([CH3:10])[O:9][CH2:8][CH:7]1[N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 120181Piperazine, hexahydrateHCID 110947474,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

Product 1

HCID 212744861-(6-Hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-piperazineYield 20.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

14.4 g (0.1 mol) of 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane (J. Org. Chem. 41, 2469 [1976]) are heated under reflux in 100 ml of acetonitrile with 20 g (0.1 mol) of piperazine hexahydrate for 8 hours and the 1,4-bis-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-piperazine precipitated [melting point: 235°-237° (from isopropanol)] is filtered off with suction. The mother liquor is concentrated and the residue is purified by chromatography on 200 g of silica gel with methylene chloride/methanol (9:1) as the mobile phase, the main component being eluted towards the end of the chromatography with methylene chloride/methanol (4:1). 4.7 g of 1-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-piperazine are obtained as an oil; Rf value=0.05 (on silica gel; methylene chloride/methanol (9:1)].

Workup

  1. customthe 1,4-bis-(6-hydroxy-2,2-dimethyl-1,3-dioxepan-5-yl)-piperazine precipitated [melting point: 235°-237° (from isopropanol)]
  2. filtrationis filtered off with suction
  3. concentrationThe mother liquor is concentrated
  4. customthe residue is purified by chromatography on 200 g of silica gel with methylene chloride/methanol (9:1) as the mobile phase
  5. washthe main component being eluted towards the end of the chromatography with methylene chloride/methanol (4:1)

Sources & evidence

ORD record
ord-128beae915bc49e894d8d706b2cffa53
Source dataset
uspto-grants-1989_02
Patent number
US04806539

Reaction notes

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