Sodium Hydroxide → HCID 20339714, compound

HRID 127733Notes

Reaction equation

HRID 127733 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][NH:26][C:27](=[O:34])[CH2:28][O:29][CH2:30][C:31]([O-:33])=[O:32])[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.[Na+].[OH-].[Na+].C([O-])(=O)COCC([O-])=O.C1(=O)OC(=O)COC1>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:27](=[O:34])[CH2:28][O:29][CH2:30][C:31]([OH:33])=[O:32])[CH2:18][CH2:19]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 782321,4-Dioxane-2,6-dioneHCID 6993564HCID 6993564, compoundHCID 23686821HCID 23686821, compound

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-piperidinohexamine 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-piperidinohexamine. To a solution of 0.685 grams (1.96 millimoles) of the thus prepared 6-piperidinohexamine in 14 milliliters of dichloromethane is added drop by drop during about 10 minutes, a warm solution of 0.227 (1.95 millimole) of diglycolic anhydride in 26 ml. 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. temperatureunder reflux temperature for 1.5 hours
  2. customto obtain 6-piperidinohexamine
  3. extractionextracted with ether
  4. washThe ether solution is washed with aqueous NaCl
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customto obtain as residue
  8. additionAfter the addition

Sources & evidence

ORD record
ord-e078cbf844784c36b187e7b7c67cc04a
Source dataset
uspto-grants-1981_03
Patent number
US04256891

Reaction notes

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