(E)-5-Dimethylamino-1-phenyl-pent-1-en-3-one; hydrochloride → 5-(Dimethylamino)-3-hydroxy-1-phenyl-1-pentene

HRID 46492Notes

Reaction equation

HRID 46492 reaction equation
Cl.[CH3:2][N:3]([CH3:16])[CH2:4][CH2:5][C:6](=[O:15])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>CO.O.O>[CH3:16][N:3]([CH3:2])[CH2:4][CH2:5][CH:6]([OH:15])[CH:7]=[CH:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 145789(E)-5-Dimethylamino-1-phenyl-pent-1-en-3-one; hydrochlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 545141025-(Dimethylamino)-3-hydroxy-1-phenyl-1-penteneYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

5-(Dimethylamino)-1-phenyl-1-penten-3-one, hydrochloride (1:1) (18.6 g, 0.078 mole) is dissolved in 200 ml 1:1 methanol-water. Sodium bicarbonate (2.0 g) is added, followed by the portionwise addition of NaBH4 (3.0 g) at 35° C. After addition, the reaction mixture is stirred for 2 hours at room temperature. This solution is diluted with 200 ml of water and organics are extracted with ether. The ether is dried with MgSO4, filtered and concentrated in vacuo to yield 14.3 g of product. IR consistent.

Workup

  1. additionAfter addition
  2. extractionorganics are extracted with ether
  3. dry with materialThe ether is dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e03dceb46aca4a64826561499e8e0c0e
Source dataset
uspto-grants-1979_11
Patent number
US04173649

Reaction notes

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