1-Methylpiperazine → 1-(4-Bromo-2-methylbenzoyl)-4-methylpiperazine

HRID 19472

Reaction equation

HRID 19472 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:40]2[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]2)=[O:8])=[C:4]([CH3:11])[CH:3]=1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 995704-Bromo-2-methylbenzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 593927541-(4-Bromo-2-methylbenzoyl)-4-methylpiperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Bromo-2-methylbenzoic acid (10 g, 46.5 mmol), and HBTU (23 g, 60.5 mmol) were dissolved in DMF (150 mL), then N-methyl piperazine (6.0 g, 60.5 mmol) and DIPEA (21 mL, 121 mmol) were added. The reaction was stirred overnight before the removal of the DMF in vacuo, the gum was quenched with 2.0N NaOH (100 mL), extracted with diethyl ether (3×200 mL), dried (MgSO4) and solvent removed in vacuo to yield a viscous gum. Purification on silica using 0-10% MeOH in DCM as eluent, gave the title compound as viscous oil. The oil was dissolved in the minimum amount of diethyl ether, iso-hexane was added to give a colourless solid which was filtered and dried (11.8 g, 86%); 1H NMR (CDCl3) 7.40 (s, 1H), 7.36 (d, 1H), 7.04 (d, 1H), 3.86-3.79 (m, 2H), 3.27-3.21 (m, 2H), 2.51-2.45 (m, 2H), 2.32-2.29 (m, 8H); MH+ 298.

Workup

  1. customthe gum was quenched with 2.0N NaOH (100 mL)
  2. extractionextracted with diethyl ether (3×200 mL)
  3. dry with materialdried (MgSO4) and solvent
  4. customremoved in vacuo
  5. customto yield a viscous gum
  6. customPurification on silica using 0-10% MeOH in DCM as eluent

Sources & evidence

ORD record
ord-737e58edd27a47cbba07fbab19ebb2d9
Source dataset
uspto-grants-2010_06
Patent number
US07745428B2

Linked notes

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