Acetic Acid → 3-((4-Methylpiperazin-1-yl)methyl)phenylboronic acid

HRID 1798546Notes

Reaction equation

HRID 1798546 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=1)=O.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([CH2:1][C:3]2[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 27343563-Formylphenylboronic acidHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 496578973-((4-Methylpiperazin-1-yl)methyl)phenylboronic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-Formylphenylboronic acid (1 eq, 2 mmol, 0.3 g) in dry DCM (7 ml) under an inert atmosphere of argon is treated with 1-methyl-piperazine (1.2 eq, 2.4 mmol, 0.266 ml) followed by acetic acid (1.2 eq, 2.4 mmol, 0.14 ml) and NaBH(OAc)3 (1.6 eq, 3.2 mmol, 0.678 mg) and the resulting mixture is stirred at room temperature for 3 hours. The reaction is quenched by addition of water and is then extracted with DCM. The organic extracts are concentrated in vacuo and the crude residue is purified by flash chromatography on silica eluting with MeOH/DCM (0 to 100% MeOH in DCM) followed by 2M NH3 in MeOH. The appropriate fractions are combined and concentrated in vacuo to afford the title compound; [M+H]+=235.

Workup

  1. customThe reaction is quenched by addition of water
  2. extractionis then extracted with DCM
  3. concentrationThe organic extracts are concentrated in vacuo
  4. customthe crude residue is purified by flash chromatography on silica eluting with MeOH/DCM (0 to 100% MeOH in DCM)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc1521ba943942a3a7f84f5aa9f07e31
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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