Acetone → 4-[4-(Propan-2-yl)piperazin-1-yl]phenol

HRID 1903094Notes

Reaction equation

HRID 1903094 reaction equation
C([BH3-])#N.[Na+].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[CH3:18][C:19]([CH3:21])=O.Cl>CO.O>[CH:19]([N:15]1[CH2:16][CH2:17][N:12]([C:9]2[CH:8]=[CH:7][C:6]([OH:5])=[CH:11][CH:10]=2)[CH2:13][CH2:14]1)([CH3:21])[CH3:18]

Participants

7

Reactant 4

HCID 180Acetone2×HCID 313Hydrochloric AcidHCID 92467p-(1-Piperazinyl)phenolHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 6890984-[4-(Propan-2-yl)piperazin-1-yl]phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Sodium cyanoborohydride (3.78 g.) was added to a stirred solution of N-(4-hydroxyphenyl)piperazine (5.35 g.) and acetone (8.7 g.) in a mixture of methanol (100 ml) and water (20 ml.). The pH of the resulting solution was adjusted to pH 7.5 by the addition of a few drops of N hydrochloric acid and stirring was continued at room temperature (~20° C.) for a period of 19 hours. Upon completion of this step, further acetone (8.7 g.) and sodium cyanoborohydride (1.89 g.) were added to the mixture and the pH was again adjusted to a value of 7.5. After a further period of stirring at room temperature for eight hours, water (100 ml.) was added to the reaction mixture and the precipitated solid product was subsequently collected by means of suction filtration and thereafter vacuum dried over phosphorous pentoxide to constant weight. Recrystallization of the crude material so obtained from a mixture of ethanol and methanol then gave pure 1-isopropyl-4-(4-hydroxyphenyl)piperazine in the form of a crystalline solid (yield, 4.78 g.), m.p. 244°-246° C. The yield of pure product amounted to 72% of the theoretical value.

Workup

  1. customwas continued at room temperature
  2. custom(~20° C.)
  3. customof 19 hours
  4. stirringAfter a further period of stirring at room temperature for eight hours
  5. filtrationthe precipitated solid product was subsequently collected by means of suction filtration
  6. dry with materialvacuum dried over phosphorous pentoxide to constant weight
  7. customRecrystallization of the crude material
  8. customso obtained from a mixture of ethanol and methanol

Sources & evidence

ORD record
ord-1627ea1e1f7e4bf7a1f179ab149b7e68
Source dataset
uspto-grants-1984_03
Patent number
US04435399

Reaction notes

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