1,4-Dioxane-2,6-dione → HCID 20339714, compound

HRID 1395479Notes

Reaction equation

HRID 1395479 reaction equation
[CH:1]([CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1(=[O:34])[O:33][C:31](=[O:32])[CH2:30][O:29][CH2:28]1>O.ClCCl>[CH:1]([CH:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:31](=[O:32])[CH2:30][O:29][CH2:28][C:27]([OH:34])=[O:33])[CH2:18][CH2:19]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 782321,4-Dioxane-2,6-dioneHCID 20339704HCID 20339704, compound2×

Product 1

HCID 20339714HCID 20339714, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A 1.02 gram (2.10 millimoles) sample of sodium {2-[6-(4-benzhydrylpiperidino)hexyl]amino-2-oxoethoxy}acetate (prepared as described in Example XIII) and 7.3 milliliters of 5 N aqueous NaOH is heated under reflux temperature for 1.5 hours to obtain 6-(4-benzhydrylpiperidino)hexanamine and diglycolate in the reaction mixture; the mixture is then diluted with 25 milliliters of water and extracted with ether. The ether solution is washed with aqueous NaCl, dried with Na2SO4, and concentrated to obtain as residue, 6-(4-benzhydrylpiperidino)hexanamine. To a solution of 0.685 gram (1.96 millimoles) of the thus prepared 6-(4-benzhydrylpiperidino)hexanamine in 14 milliliters of dichloromethane is added drop by drop during about 10 minutes, a warm solution of 0.227 gram (1.95 millimole) of diglycolic anhydride in 26 milliliters of dichloromethane. After the addition, the mixture is stirred at a temperature range of 25°-30° C. for two hours to obtain the desired {2-[ 6-(4-benzhydrylpiperidino)hexyl]amino-2-oxoethoxy}acetic acid; the latter is isolated by volatilization of the solvent.

Workup

  1. extractionextracted with ether
  2. washThe ether solution is washed with aqueous NaCl
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customto obtain as residue
  6. additionAfter the addition

Sources & evidence

ORD record
ord-654a7fb2b6a4453d9c97e1e0015cc714
Source dataset
uspto-grants-1980_05
Patent number
US04203991

Reaction notes

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