Acetic Acid → 1-(4-Bromophenyl)-4-isopropylpiperazine

HRID 447330

Reaction equation

HRID 447330 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:14][C:15]([CH3:17])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:15]([CH3:17])[CH3:14])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 27356291-(4-Bromophenyl)piperazineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 114033311-(4-Bromophenyl)-4-isopropylpiperazineYield 99%

Reagents, catalysts & solvents 1

HCID 21493386Dce thfSolvent

Procedure

To a mixture of 1-(4-bromophenyl)piperazine (1.20 g, 5 mmol) and acetone (1.47 mL, 20 mmol) in DCE/THF (45 mL/15 mL) was added NaBH(OAc)3 (1.38 g, 6.5 mmol), followed by AcOH (0.5 mL). After addition, the resulting mixture was stirred O/N at rt. The reaction as quenched with NaHCO3 (10 mL) and H2O (10 mL), and was extracted with EtOAc (60 mL×2). The solvents were removed in vacuo to give the crude title compound as a white solid (1.40 g, 99%). 1H NMR (400 MHz, DMSO-d6) δ 7.45 (d, J=7.2 Hz, 2H), 7.21 (d, J=7.2 Hz, 2H), 3.64-3.55 (m, 2H), 3.44 (s, 2H), 2.68 (d, J=11.6 Hz, 2H), 1.75 (t, J=11.0 Hz, 2H), 1.54 (d, J=6.0 Hz, 6H); MS ESI 282.9 [M+H]+, calcd. for [C13H19BrN2+H]+ 283.1.

Workup

  1. additionAfter addition
  2. customThe reaction
  3. customas quenched with NaHCO3 (10 mL) and H2O (10 mL)
  4. extractionwas extracted with EtOAc (60 mL×2)
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-ffc87ca68d7a4e6e964702f194c2eccc
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Linked notes

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