Piperazine → Benzhydrylpiperazine

HRID 1406659Notes

Reaction equation

HRID 1406659 reaction equation
Cl[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C1COCC1>[CH:2]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 7035Chlorodiphenylmethane

Product 1

HCID 70048Benzhydrylpiperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: chlorodiphenylmethane (4{23}, 5 mL, 28.1 mmol, 1 equiv.), piperazine (14.5 g, 168.7 mmol, 6 equiv.), THF (61.4 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{23} (5.12 g, 72%) as a light yellow solid. 1H-NMR (500 MHz, CDCl3): δ 7.43 (d, 4H, J=7.0 Hz), 7.28 (t, 4H, J=7.5 Hz), 7.18 (t, 2H, J=7.5 Hz), 4.22 (s, 1H), 2.88 (t, 4H, J=5.0 Hz), 2.36 (br s, 4H), 1.46 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 142.6, 128.3, 127.9, 126.7, 76.7, 53.3, 46.3.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{23} (5.12 g, 72%) as a light yellow solid

Sources & evidence

ORD record
ord-33f193f292f945bbb138d6bddcc992e0
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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