Acetic Acid → 1-Cyclopentyl-4-(4-iodophenyl)piperazine

HRID 447326

Reaction equation

HRID 447326 reaction equation
[I: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.[C:14]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl.C1COCC1>[CH:14]1([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 41478451-(4-Iodophenyl)piperazineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 584862611-Cyclopentyl-4-(4-iodophenyl)piperazineYield 82%

Reagents, catalysts & solvents 1

HCID 21493386Dce thfSolvent

Procedure

To a mixture of 1-(4-iodophenyl)piperazine (1.44 g, 5 mmol) and cyclopentanone (840 mg, 10 mmol) in DCE/THF (40 mL/20 mL) was added NaBH(OAc)3 (1.484 g, 7 mmol), followed by AcOH (0.5 mL). After addition, the resulting mixture was stirred 22 h at rt. After quenching with sat. NaHCO3 (20 mL), H2O (20 mL) and brine (20 mL), the solution was extracted with EtOAc (60 mL+30 mL). Removal of solvents, followed by trituration with MeOH afforded the crude title compound as a pale yellow solid (1.46 g, 82%). 1H NMR (400 MHz, DMSO-d6) δ 7.52 (d, J=8.4 Hz, 2H), 6.70 (d, J=8.4 Hz, 2H), 3.20 (t, J=4.8 Hz, 4H), 2.66 (t, J=4.6 Hz, 4H), 2.54 (p, J=7.6 Hz, 1H), 1.96-1.87 (m, 2H), 1.78-1.52 (m, 4H), 1.50-1.38 (m, 2H); MS ESI 357.0 [M+H]+, calcd. for [C15H21IN2+H]+ 357.1.

Workup

  1. additionAfter addition
  2. customAfter quenching with sat. NaHCO3 (20 mL), H2O (20 mL) and brine (20 mL)
  3. extractionthe solution was extracted with EtOAc (60 mL+30 mL)
  4. customRemoval of solvents

Sources & evidence

ORD record
ord-2d8ed16d81ed451eb9f8b6b6b63aca75
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Linked notes

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