Acetyl chloride → (2R,5S)-1-Acetyl-2,5-dimethyl-4-(4-nitrophenyl)piperazine

HRID 1441360Notes

Reaction equation

HRID 1441360 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.[C:18](Cl)(=[O:20])[CH3:19]>>[C:18]([N:6]1[CH2:7][C@H:2]([CH3:1])[N:3]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH2:4][C@H:5]1[CH3:8])(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 57664370(2S,5R)-2,5-Dimethyl-1-(4-nitrophenyl)piperazine

Product 1

HCID 68686760(2R,5S)-1-Acetyl-2,5-dimethyl-4-(4-nitrophenyl)piperazine

Procedure

The title compound was prepared from (2S,5R)-2,5-dimethyl-1-(4-nitrophenyl)piperazine (Method 28, 8.22 g, 34.95 mmol) and acetyl chloride (4.5 ml, 62.91) by the procedure of Method 26. It was obtained as an oil which solidified on standing overnight (11.39 g, >100%, contaminated with solvent) NMR (400 MHz) 1.13 (m, 6H), 3.07 (m, 1H), 3.33 (m, 1H), 3.68 (m, 1H), 4.25 (m, 2H), 4.69 (m, 1H), 7.00 (d, 2H), 8.05 (d, 2H); m/z 278.

Workup

  1. customIt was obtained as an oil which

Sources & evidence

ORD record
ord-9c492de619204a849626a739f798695f
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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