Hydrochloric Acid → 3-(1-Benzyl-piperidin-4-ylamino)-propan-1-ol

HRID 352439Notes

Reaction equation

HRID 352439 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[OH-].[Na+]>C(Cl)Cl>[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 90863-Amino-1-propanolHCID 14798Sodium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 31534663-(1-Benzyl-piperidin-4-ylamino)-propan-1-olYield 58.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16.5 g of 3-aminopropanol and 41.7 g of 1-benzyl-4-piperidone are dissolved in 350 ml of methylene chloride and 56 g of sodium triacetoxy-borohydride are slowly added at about 10° C. The mixture is stirred overnight at ambient temperature, then acidified with dilute hydrochloric acid while cooling and then made alkaline with conc. sodium hydroxide solution. The organic phase is separated off, the aqueous phase is washed once more with 150 ml of methylene chloride. The combined organic phases are dried over sodium sulphate and the solvent is eliminated in vacuo. 32 g of 1-benzyl-4-(3-hydroxy-propylamino)-piperidine are obtained as a yellow oil, which is used without further purification in the next reaction step.

Workup

  1. temperaturewhile cooling
  2. customThe organic phase is separated off
  3. washthe aqueous phase is washed once more with 150 ml of methylene chloride
  4. dry with materialThe combined organic phases are dried over sodium sulphate

Sources & evidence

ORD record
ord-6711517e198747158f0c905f5ff645b6
Source dataset
uspto-grants-2004_06
Patent number
US06747044B2

Reaction notes

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