Piperazine → HCID 18436722, compound

HRID 456471Notes

Reaction equation

HRID 456471 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][C:10]([CH3:15])([N+:12]([O-:14])=[O:13])[CH3:11].[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1>[CH3:11][C:10]([N+:12]([O-:14])=[O:13])([CH3:15])[CH2:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 634876Binap, (A+-)-HCID 17952560HCID 17952560, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 18436722HCID 18436722, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-bromo-2-(2-methyl-2-nitro-propoxy)-benzene (2.30 g, 8.4 mmol), piperazine (1.8 g, 20 mmol), Pd2dba2 (384 mg, 0.4 mmol), BINAP (784 mg, 1.26 mmol), and NaOtBu (1.13 g, 12 mmol) in 34 mL of toluene was heated to 90° C. for 5 hrs. The solution was concentrated, dissolved in CH2Cl2 and filtered through celite. Purification by silica gel chromatography (4×20 cm SiO2, 0,1,2,3,4,5,7,9,11% 2M NH3 in MeOH/CH2Cl2 step gradient, 12 min each at 35 mL/min) afforded 1.72 g (6.15 mmol, 73%) of 1-[2-(2-methyl-2-nitro-propoxy)-phenyl]-piperazine as a yellow oil. LRMS (electrospray): 280.1 [M+1].

Workup

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in CH2Cl2
  3. filtrationfiltered through celite
  4. customPurification by silica gel chromatography (4×20 cm SiO2, 0,1,2,3,4,5,7,9,11% 2M NH3 in MeOH/CH2Cl2 step gradient, 12 min each at 35 mL/min)

Sources & evidence

ORD record
ord-ffa2938a5d204d4db978e649babdb950
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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