Hydrochloric Acid → HCID 22712056, compound

HRID 1167585Notes

Reaction equation

HRID 1167585 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 methylene chloride and at 0° C. combined with 21.2 g of sodium triacetoxyborohydride. The mixture is stirred overnight 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 over silica gel with ethyl acetate/methanol/conc. ammonia solution 20:80:1. The uniform fractions according to TLC are combined and freed from solvent 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 over silica gel with ethyl acetate/methanol/conc

Sources & evidence

ORD record
ord-2c6a2f891ce8490cb046d2f71f197a8b
Source dataset
uspto-grants-2003_09
Patent number
US06620438B2

Reaction notes

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