Potassium Sodium Tartrate → 4-(Aminomethyl)-1-benzylpiperidin-4-ol

HRID 2407749Notes

Reaction equation

HRID 2407749 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:16])([C:14]#[N:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[NH2:15][CH2:14][C:11]1([OH:16])[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 801891-Benzyl-4-hydroxypiperidine-4-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 104210264-(Aminomethyl)-1-benzylpiperidin-4-olYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of the compound prepared in Example 248 (4.00 g) in tetrahydrofuran (90 mL) was treated with lithium aluminum hydride (1.75 g) slowly at 0° C. The mixture was allowed to stir at room temperature overnight, cooled to 0° C. and treated with Rochelle's salt (sodium potassium tartrate; 400 g). After stirring at room temperature for 3 hours, the organic phase was separated and the aqueous layer extracted with ethyl acetate. The combined organic extracts were dried and evaporated in vacuo to obtain the title compound (3.76 g) having the following physical data.

Workup

  1. temperaturecooled to 0° C.
  2. stirringAfter stirring at room temperature for 3 hours
  3. customthe organic phase was separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. customThe combined organic extracts were dried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-30f980b94a2c45e0b076b64c5c4cfd72
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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