Acetic Acid → HCID 79673114, compound

HRID 589474Notes

Reaction equation

HRID 589474 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=O.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][N:15]1[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5003444Sodium cyanoborohydrideHCID 219862463-Bromo-5-fluorobenzaldehyde

Product 1

HCID 79673114HCID 79673114, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-bromo-5-fluorobenzaldehyde (CI) (2.12 g, 10.42 mmol) in MeOH (200 mL) was added 1-methylpiperazine (2.3 mL, 20.84 mL). The pH was adjusted to 6 using HOAc and stirred for 1 h. NaCNBH3 (917 mg, 14.59 mmol) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and evaporated under vacuum. The crude product was purified on a silica gel column (100% CHCl3→3:97 MeOH[7N NH3]:CHCl3) to produce 1-(3-bromo-5-fluorobenzyl)-4-methylpiperazine (CII) as a yellow oil (1.52 g, 5.29 mmol, 51% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 2.14 (s, 3H), 2.28-2.40 (m, 8H), 3.46 (s, 2H), 7.15-7.17 (m, 1H), 7.35 (s, 1H), 7.40-7.42 (m, 1H); ESIMS found C12H16BrFN2 m/z 287 (M+H).

Workup

  1. stirringstirred at room temperature overnight
  2. customThe MeOH was removed under vacuum
  3. customthe residue was partitioned between CHCl3 and saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated under vacuum
  6. customThe crude product was purified on a silica gel column (100% CHCl3→3:97 MeOH[7N NH3]:CHCl3)

Sources & evidence

ORD record
ord-630900bcfc7a42cd9ff7ad60734f5ea9
Source dataset
uspto-grants-2016_01
Patent number
US09233104B2

Reaction notes

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