Sodium Hydroxide → 3-(Dimethylamino)-1-(2-thienyl)-1-propanol

HRID 1031993

Reaction equation

HRID 1031993 reaction equation
Cl.[CH3:2][N:3]([CH3:13])[CH2:4][CH2:5][C:6]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)=[O:7].[OH-].[Na+].[BH4-].[Na+]>CO.O>[CH3:13][N:3]([CH3:2])[CH2:4][CH2:5][CH:6]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[OH:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 28768913-(Dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 115864093-(Dimethylamino)-1-(2-thienyl)-1-propanolYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-dimethylamino-1-(2-thienyl)-1-propanone hydrochloride (70.0 g, 0.34 mol) in 840 ml of methanol and 420 ml of water at about 0° C. was added 5N sodium hydroxide until the solution was slightly basic. To the resulting solution was added sodium borohydride (12.9 g., 0.34 mol) in portions. The mixture was allowed to warm to room temperature overnight. The methanol was removed in vacuo and the remaining solution was diluted with water. The solution was extracted with diethyl ether, and the solution was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to provide 56.7 g of colorless crystals. Recrystallization of the crystals from hexanes gave 49.24 g (78%) of the title compound as colorless crystals mp=72° C.-74° C.

Workup

  1. customThe methanol was removed in vacuo
  2. additionthe remaining solution was diluted with water
  3. extractionThe solution was extracted with diethyl ether
  4. washthe solution was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-523cc4084ed64cca9b3dcca9532e11ad
Source dataset
uspto-grants-1990_09
Patent number
US04956388

Linked notes

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