Water → 1,3-Bis[4-(4-bromobenzoyl)-1-piperazinyl]propane

HRID 1006234Notes

Reaction equation

HRID 1006234 reaction equation
Cl.[Br:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[C:17](=[O:20])([O-])[O-].[Na+].[Na+].O.O.[CH:25](O)([CH3:27])[CH3:26]>CN(C)C=O.BrCCCBr>[Br:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH2:26][CH2:25][CH2:27][N:9]3[CH2:10][CH2:11][N:12]([C:17](=[O:20])[C:6]4[CH:15]=[CH:16][C:3]([Br:2])=[CH:4][CH:5]=4)[CH2:13][CH2:14]3)[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 21889133Propan-2-ol--water (1/1)HCID 226768571-(4-Bromobenzoyl)piperazine hydrochloride

Product 1

HCID 116927231,3-Bis[4-(4-bromobenzoyl)-1-piperazinyl]propane

Reagents, catalysts & solvents 2

HCID 80011,3-DibromopropaneCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 66.7 g (0.218 mmol) of the 1-(4-bromobenzoyl)piperazine hydrochloride prepared in Preparation Example 1 in dimethylformamide (223 mL) were added 11.3 mL (98% purity, 0.109 mmol) of 1,3-dibromopropane and 33.5 g (0.316 mmol) of sodium carbonate. The mixture was stirred for 6 hours at 80° C. Water (670 mL) was added to the reaction mixture with stirring at 80° C. and the mixture was stirred for 0.5 hour at the same temperature and for 1.5 hours at 20° C. The precipitates were collected by filtration and washed with water (3×45 mL) to obtain crude crystals. A suspension of the crude crystals in water-isopropanol (7:3, 570 mL) was stirred for 2 hours at 85° C., for 0.5 hour at room temperature, and for 1 hour at 0° C. Precipitated crystals were collected by filtration and washed with water-isopropanol (5:1, 2×110 mL), whereby 60.0 g of 1,3-bis[4-(4-bromobenzoyl)-1-piperazinyl]propane was obtained as colorless fine needles (yield 95%).mp: 170.0 to 173.0° C.

Workup

  1. stirringwith stirring at 80° C.
  2. stirringthe mixture was stirred for 0.5 hour at the same temperature and for 1.5 hours at 20° C
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water (3×45 mL)
  5. customto obtain crude crystals
  6. stirringwas stirred for 2 hours at 85° C., for 0.5 hour at room temperature
  7. waitfor 1 hour at 0° C
  8. customPrecipitated crystals
  9. filtrationwere collected by filtration
  10. washwashed with water-isopropanol (5:1, 2×110 mL)

Sources & evidence

ORD record
ord-401c845db38743d9a76630930b7abad7
Source dataset
uspto-grants-2004_09
Patent number
US06787653B2

Reaction notes

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