Hydrochloric Acid → HCID 22712056, compound

HRID 352436Notes

Reaction equation

HRID 352436 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][OH:8].[CH2:9]([N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[OH-].[Na+]>C(Cl)Cl>[CH2:9]([N:16]1[CH2:21][CH2:20][CH:19]([N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6][CH2:7][OH:8])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 30150593-((2-Hydroxyethyl)amino)propanolHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22712056HCID 22712056, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6 g of 2-hydroxyethyl-3-hydroxypropylamine and 18,9 g of 1-benzyl-4-piperidone are taken up in 250 ml of methylene chloride and combined at 0° C. with 21.2 g of sodium triacetoxyborohydride. The mixture is stirred over night at ambient temperature, then acidified with 2 N hydrochloric acid and made alkaline with concentrated sodium hydroxide solution. It is extracted with methylene chloride, the extract is dried over sodium sulphate and the solvent is eliminated in vacuo. The residue is chromatographed with ethyl acetate/methanol/conc. ammonia solution 20:80:1 over silica gel. The fractions found to be uniform by TLC are combined and the solvent is eliminated in vacuo. 2.3 g of 1-benzyl-4-[(2-hydroxy-ethyl)-(3-hydroxy-propyl)-amino]-piperidine are obtained as an oil.

Workup

  1. extractionIt is extracted with methylene chloride
  2. dry with materialthe extract is dried over sodium sulphate
  3. customThe residue is chromatographed with ethyl acetate/methanol/conc

Sources & evidence

ORD record
ord-4c6545431c7945f394a4c3ba1250275e
Source dataset
uspto-grants-2004_06
Patent number
US06747044B2

Reaction notes

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