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

HRID 1167588Notes

Reaction equation

HRID 1167588 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 methylene chloride and at about 10° C. 56 g of sodium triacetoxy-borohydride are slowly added. The mixture is stirred overnight at ambient temperature, then acidified with dilute hydrochloric acid with cooling and subsequently made alkaline with conc. sodium hydroxide solution. The organic phase is separated off, the aqueous phase is washed once again with 150 ml of methylene chloride. The combined organic phases are dried over sodium sulphate and freed from solvent in vacuo. 32 g 1-benzyl-4-(3-hydroxy-propylamino)-piperidine are obtained as a yellow oil which is used in the next reaction step without any further purification.

Workup

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

Sources & evidence

ORD record
ord-358fd5966c174100b04c06c091c75c3b
Source dataset
uspto-grants-2003_09
Patent number
US06620438B2

Reaction notes

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