Acetonitrile → HCID 22458184, compound

HRID 1420571Notes

Reaction equation

HRID 1420571 reaction equation
B(Br)(Br)Br.[C:5]1([NH:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])[CH2:16][CH2:15]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:28](#N)[CH3:29].C([O-])([O-])=[O:32].[Na+].[Na+]>C(Cl)Cl>[C:28]([C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH2:18][CH2:19]1)(=[O:32])[CH3:29]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 22458110HCID 22458110, compound

Product 1

HCID 22458184HCID 22458184, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-3 °C

Procedure

A solution of 1M boron tribromide in CH2Cl2 (2.37 mL) was dropped into another solution containing 0.74 g of 1-(N-phenyl-2-aminoethyl)-4-(2-methoxyphenyl) piperazine in 10 mL of CH2Cl2 stirred at -3° C. in nitrogen atmosphere. Subsequently, 0.25 mL of acetonitrile at room temperature was added and the mixture was stirred for 1 h at room temperature and for 8 h until precipitation. After cooling at room temperature, the mixture was treated with a 10% aqueous solution of Na2CO3 and the organic phase that separated was dried on anhydrous Na2SO4 and evaporated to dryness. The crude was purified via flash chromatography (CH2Cl2 --MeOH 98:2) and the residue crystallized from EtOH giving 0.33 g (39%) of the title compound. Melting point: 92-94° C.

Workup

  1. stirringthe mixture was stirred for 1 h at room temperature and for 8 h until precipitation
  2. temperatureAfter cooling at room temperature
  3. customthe organic phase that separated
  4. dry with materialwas dried on anhydrous Na2SO4
  5. customevaporated to dryness
  6. customThe crude was purified via flash chromatography (CH2Cl2 --MeOH 98:2)
  7. customthe residue crystallized from EtOH giving 0.33 g (39%) of the title compound

Sources & evidence

ORD record
ord-de2c57f9567d445b8a6aa19244715ed4
Source dataset
uspto-grants-2000_06
Patent number
US06071920

Reaction notes

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