Hydrochloric Acid → HCID 14257855, compound

HRID 2231714Notes

Reaction equation

HRID 2231714 reaction equation
[ClH:1].[C:2]1([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH:16]=[O:17])[CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O(C)[Na].[BH4-].[Na+].Cl>C(O)C.CO.CCOC(C)=O>[ClH:1].[CH3:8][C:2]1[CH:7]=[CH:6][C:5]([CH:16]([CH:13]2[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][CH2:12]2)[OH:17])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86742524HCID 86742524, 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 mixutre 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 and 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 CH3OH to give alpha(4-methylphenyl)- 1-(2-phenylethyl)-4-piperidinemethanol hydrochloride, mp 181°-183° C.

Workup

  1. concentrationThe reaction mixutre was concentrated to a solid
  2. extractionThe mixture was extracted with CH2Cl2 (3×50 ml)
  3. washThe CH2Cl2 solution was washed with water
  4. dry with materialsaturated NaCl solution, and dried 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 CH3OH

Sources & evidence

ORD record
ord-a7e0f9c3416e44f9a4fa49686cf0c494
Source dataset
uspto-grants-1988_11
Patent number
US04783471

Reaction notes

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