Water → HCID 57733055, compound

HRID 1014953Notes

Reaction equation

HRID 1014953 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:15][CH2:14]2)[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br.O.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:17][CH2:18]2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 9907323Cutamesine

Product 1

HCID 57733055HCID 57733055, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine (0.829 g, 2.25 mmol) in dichloromethane (DCM, 20 mL) is added boron tribromide (BBr3) drop wise at −78° C. under nitrogen. After the addition had been completed, the reaction solution is slowly warmed to 0° C., stirred for 5 h and then cooled to −10° C. To the cooled reaction mixture is added water cautiously. The resulting mixture is neutralised with sodium bicarbonate at ambient temperature and extracted with ethyl acetate/THF. The organic layer is separated, filtered through silica gel, dried over sodium sulfate, concentrated, and dried in a vacuum oven. The residue is then purified by column chromatography eluting with dichloromethane-methanol to afford 0.57 g of 1-[2-(3,4-dihydroxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine. This material is then dissolved in ethanol and treated with 6 N hydrogen chloride aqueous solution to pH=3. The resultant crystals are filtered, washed with cold ethanol, and dried to give 212 mg of the title compound (25% from 1-[2-(3,4-dimethoxyphenyl)ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride).

Workup

  1. additionAfter the addition
  2. temperaturecooled to −10° C
  3. customTo the cooled reaction mixture
  4. extractionextracted with ethyl acetate/THF
  5. customThe organic layer is separated
  6. filtrationfiltered through silica gel
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customdried in a vacuum oven
  10. customThe residue is then purified by column chromatography
  11. washeluting with dichloromethane-methanol

Sources & evidence

ORD record
ord-5e2c62d26e724e2588f25ccfba8e6831
Source dataset
uspto-grants-2011_07
Patent number
US07985751B2

Reaction notes

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