1-(Isopropyl)-4-piperidone → 1-Isopropylpiperidin-4-ol

HRID 1294818Notes

Reaction equation

HRID 1294818 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 793131-(Isopropyl)-4-piperidoneHCID 4311764Sodium borohydride

Product 1

HCID 796811-Isopropylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-isopropyl-piperidin-4-one (51.2 g) in absolute ethanol (350 mL) was treated with sodium borohydride (7.30 g) at a rate not to exceed an internal temperature of 50° C. After 48 h, the solvent was evaporated and the resulting yellow paste was partitioned between DCM (300 mL) and 5% NaOH (300 mL). This mixture was stirred for 6 h and then extracted with DCM (4×100 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Distillation of the yellow oil (bp 68° C., 1.5 mm Hg) gave the title compound as an off-white waxy solid (35.3 g).

Workup

  1. customan internal temperature of 50° C
  2. customthe solvent was evaporated
  3. customthe resulting yellow paste was partitioned between DCM (300 mL) and 5% NaOH (300 mL)
  4. extractionextracted with DCM (4×100 mL)
  5. dry with materialThe combined organic phases were dried (sodium sulfate)
  6. customevaporated
  7. distillationDistillation of the yellow oil (bp 68° C., 1.5 mm Hg)

Sources & evidence

ORD record
ord-ea6cbb57494f459fa007f0b190c9193a
Source dataset
uspto-grants-2007_07
Patent number
US07241778B2

Reaction notes

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