Piperazine → Benzhydrylpiperazine

HRID 223455Notes

Reaction equation

HRID 223455 reaction equation
[C:1]1([CH:7](Br)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[I-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:1]1([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 236603Bromodiphenylmethane

Product 1

HCID 70048BenzhydrylpiperazineYield 11.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of diphenylmethyl bromide (40 g, 0.16 mol), piperazine (27.8 g, 0.32 mol), potassium iodide (26.8 g, 0.16 mol) and sodium carbonate (86 g, 0.81 mol) in toluene (400 ml) was heated at reflux for 3.5 hr. The reaction mixture was filtered. The filtrate was evaporated to dryness to give 40 g of crude product. The crude product was purified by chromatography using 10% methanol in chloroform as the eluant. Pooling of the appropriate fractions gave 4.5 g of the title compound, NMR (CDCl3) δ1.82 (s,1H), 2.3(t,J=5 Hz,4H), 2.85 (t,J=5 Hz, 4H), 4.2 (s,1H), 7.3 (m,10H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hr
  3. filtrationThe reaction mixture was filtered
  4. customThe filtrate was evaporated to dryness
  5. customto give 40 g of crude product
  6. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-56528d9e3894409ea08f8ee6c0a073de
Source dataset
uspto-grants-1982_10
Patent number
US04355031

Reaction notes

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