Calcium Chloride → (+)-Trans-1-methyl-3-hydroxymethyl-4-(3,4-dichlorophenyl)-piperidine

HRID 227571Notes

Reaction equation

HRID 227571 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[C@H:4]([CH2:16][OH:17])[CH2:3]1.CC(C)([O-])C.[K+].[Cl-].[Cl-].[Ca+2]>CN(C)C=O>[CH3:1][N:2]1[CH2:7][CH2:6][C@@H:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[C@H:4]([CH2:16][OH:17])[CH2:3]1

Participants

5

Reactant 3

HCID 5284359Calcium ChlorideHCID 9860329HCID 9860329, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 68533629(+)-Trans-1-methyl-3-hydroxymethyl-4-(3,4-dichlorophenyl)-piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (5) (10.0 g, 36 mmol) and potassium tert-butoxide (12.0 g, 1.08 mmol) in dimethylformamide (75 ml) was stirred over night. CaCl2 (75 ml, 3M) was added and the reaction mixture was extracted with ethyl acetate (2×200 ml). The combined organic phases was dried with sodium sulfate and evaporated to dryness. The residue was recrystallized from ethyl acetate (7 ml). Yield 6.3 g (63%) of (7), mp 137-139° C., [α]D25=+39°.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (2×200 ml)
  2. dry with materialThe combined organic phases was dried with sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was recrystallized from ethyl acetate (7 ml)

Sources & evidence

ORD record
ord-f51fadeb3a3a4225b015768e7dcab3c7
Source dataset
uspto-grants-2009_07
Patent number
US07560562B2

Reaction notes

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