Acetone → HCID 19699952, compound

HRID 863202Notes

Reaction equation

HRID 863202 reaction equation
[OH:1][CH:2]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[CH3:3].[CH3:19][NH2:20].[BH4-].[Na+].CC(C)=O>CO.O>[CH3:19][NH:20][CH2:13][C:12]1[CH:15]=[CH:16][C:9]([CH2:8][C:7]2[CH:17]=[CH:18][C:4]([CH:2]([OH:1])[CH3:3])=[CH:5][CH:6]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 6329MethylamineHCID 4311764Sodium borohydride2×HCID 19699936HCID 19699936, compound

Product 1

HCID 19699952HCID 19699952, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

9.8 g of the 4-[4-(1-hydroxyethyl)benzyl]benzaldehyde prepared in the step (c) and 3.7 ml of methylamine (40% methanolic solution) were stirred together in 20 ml of methanol at room temperature. After one hour, the resulting mixture was cooled with ice, followed by the addition of 0.93 g of sodium borohydride. The obtained mixture was stirred at room temperature for 30 minutes. 5 ml of acetone was dropwise added to the resulting mixture under cooling with ice to treat excess sodium borohydride therewith. The reaction mixture was poured into water and the resulting mixture was extracted with dichloromethane. The organic phase was washed with water and a saturated aqueous solution of common salt, dried and distilled to dryness. The residue was recrystallized from ether/isopropyl ether to give 10.2 g of the title compound as a colorless solid.

Workup

  1. temperaturethe resulting mixture was cooled with ice
  2. temperatureunder cooling with ice
  3. extractionthe resulting mixture was extracted with dichloromethane
  4. washThe organic phase was washed with water
  5. customa saturated aqueous solution of common salt, dried
  6. distillationdistilled to dryness
  7. customThe residue was recrystallized from ether/isopropyl ether

Sources & evidence

ORD record
ord-328a736dbba2420d9c02cccf7d6a84de
Source dataset
uspto-grants-1998_02
Patent number
US05719303

Reaction notes

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