HCID 743271, compound → HCID 18790269, compound

HRID 1106948Notes

Reaction equation

HRID 1106948 reaction equation
B#B.[Cl:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=O)[CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1>C1COCC1>[ClH:3].[Cl:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:14][CH2:15]2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 743271HCID 743271, compoundHCID 6328200Diboron

Product 1

HCID 18790269HCID 18790269, compoundYield 132.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of diborane:dimethyl sulfide complex (2M) in THF (30 mL) was added drop wise a solution of dry THF (25 mL) and 1-(3-chlorophenyl)-4-(3-phenylpropionyl)piperazine (1.28 g, 3.86 mmol). The reaction mixture was stirred at room temperature for 18 h, quenched by the addition of MeOH-HCl (25 mL), and the solvents removed under reduced pressure. Additional MeOH was added and removed under reduced pressure to give a tan solid. This was dried for 18 h under vacuum then recrystallized from MEK to give 0.9 g (67%) of colorless crystals, mp 168-169° C.

Workup

  1. customquenched by the addition of MeOH-HCl (25 mL)
  2. customthe solvents removed under reduced pressure
  3. additionAdditional MeOH was added
  4. customremoved under reduced pressure
  5. customto give a tan solid
  6. customThis was dried for 18 h under vacuum
  7. customthen recrystallized from MEK

Sources & evidence

ORD record
ord-25b3da905c3f455aad150b6aee68d081
Source dataset
uspto-grants-2000_05
Patent number
US06057371

Reaction notes

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