Hydrochloric Acid → HCID 14257855, compound

HRID 1493191Notes

Reaction equation

HRID 1493191 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:5][CH:4]=1.O(C)[Na].[BH4-].[Na+].Cl>C(O)C.CO.CCOC(C)=O>[ClH:1].[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:16]2)[OH:10])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 14257841HCID 14257841, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 14257855HCID 14257855, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of (4-methylphenyl)[1-(2-phenylethyl)-4-piperidinyl]-methanone hydrochloride (9.5 g, 0.028 mol) in absolute ethanol (350 ml) was treated first by the addition of NaOCH3 (1.62 g, 0.03 mol) and then, portionwise, with sodium borohydride (2.27 g, 0.06 mol) and stirred at room temperature for 18 h. The reaction mixture was concentrated to a solid and stirred with 10% aqueous NaOH. The mixture was extracted with CH2Cl2 (3×50 ml). The CH2Cl2 solution was washed with water a then saturated NaCl solution, and dried over Na2SO4. After filtering off the Na2SO4, the filtrate was concentrated to a solid. This material was dissolved in EtOAc/Et2O (1:1, 200 ml) and treated with a solution of HCl (0.023 mol) in CH3OH/EtOAc (3:10, 13 ml). The resulting precipitate was twice recrystallized from butanone containing a small amount of CH30OH to give alpha-(4-methylphenyl)- 1-(2-phenylethyl) -4-piperidinemethanol hydrochloride, mp 181°-183° C.

Workup

  1. concentrationThe reaction mixture was concentrated to a solid
  2. extractionThe mixture was extracted with CH2Cl2 (3×50 ml)
  3. washThe CH2Cl2 solution was washed with water a then saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtering off the Na2SO4
  6. concentrationthe filtrate was concentrated to a solid
  7. dissolutionThis material was dissolved in EtOAc/Et2O (1:1, 200 ml)
  8. customThe resulting precipitate was twice recrystallized from butanone containing a small amount of CH30OH

Sources & evidence

ORD record
ord-2a0f252ebd33413a9eca8b4f6742b817
Source dataset
uspto-grants-1991_06
Patent number
US05021428

Reaction notes

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