Formaldehyde → 1-Methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)piperazine

HRID 1052301Notes

Reaction equation

HRID 1052301 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][C:16]1([CH3:35])[C:20]([CH3:22])([CH3:21])[O:19][B:18]([C:23]2[CH:24]=[C:25]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[CH:26]=[CH:27][CH:28]=2)[O:17]1.C=O>C(Cl)Cl>[CH3:1][N:32]1[CH2:31][CH2:30][N:29]([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([B:18]3[O:17][C:16]([CH3:35])([CH3:15])[C:20]([CH3:21])([CH3:22])[O:19]3)[CH:24]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 450522281-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine

Product 1

HCID 592647461-Methyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium triacetoxyborohydride (0.066 g, 0.31 mmol) was added to a solution of 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine (60.0 mg, 0.208 mmol, from Boron Molecular) and 11.0 M aqueous formaldehyde (0.057 mL, 0.62 mmol) in methylene chloride (0.8 mL, 10 mmol) and then the reaction was stirred at r.t. for 1 hour. The mixture was diluted with methylene chloride, washed with saturated NaHCO3, water, brine, then dried over Na2SO4, filtered and concentrated to provide the product which was used in the next step. LCMS calculated for C17H28BN2O2 (M+H)+: m/z=303.2. Found 303.2.

Workup

  1. washwashed with saturated NaHCO3, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide the product which

Sources & evidence

ORD record
ord-d1b9fd99fee54401a43da46430753b85
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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