Piperazine → HCID 4554455, compound

HRID 1406637Notes

Reaction equation

HRID 1406637 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C1COCC1>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 932913-Phenoxybenzyl chloride

Product 1

HCID 4554455HCID 4554455, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 3-phenoxybenzyl chloride (4{11}, 5 g, 22.9 mmol, 1 equiv.), piperazine (11.8 g, 137.2 mmol, 6 equiv.), THF (6.14 mL). Purification with flash column chromatography on silica gel (gradient, 4:1 to 1:4 EtOAc:MeOH) afforded 5{11} (5.72 g, 93%) as a light yellow oil. 1H-NMR (500 MHz, CDCl3): δ 7.35-7.32 (m, 2H) 7.28 (d, 1H, J=8.5 Hz), 7.12-7.08 (m, 2H), 7.05 (br s, 1H), 7.02 (d, 2H, J=8.0 Hz), 6.90 (dd, 1H, J=2.0, 8.0 Hz), 3.48 (s, 2H), 2.88 (t, 4H, J=5.0 Hz), 2.42 (br s, 4H), 1.66 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 157.2, 156.9, 140.2, 129.5, 129.2, 123.8, 122.9, 119.5, 118.5, 117.3, 63.1, 54.3, 45.9.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (gradient, 4:1 to 1:4 EtOAc:MeOH)
  3. customafforded 5{11} (5.72 g, 93%) as a light yellow oil

Sources & evidence

ORD record
ord-e16ce0a3d39c46e4b9aad690830c9872
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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