Acetyl chloride → (2R,6S)-1-Acetyl-2,6-dimethyl-4-(4-nitrophenyl)piperazine

HRID 1441359Notes

Reaction equation

HRID 1441359 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH2:3]1.[C:18](Cl)(=[O:20])[CH3:19]>>[C:18]([N:7]1[C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH2:3][C@H:2]1[CH3:1])(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 7059963cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazine

Product 1

HCID 68685853(2R,6S)-1-Acetyl-2,6-dimethyl-4-(4-nitrophenyl)piperazine

Procedure

The title compound was prepared from (3R,5S)-3,5-dimethyl-1-(4-nitrophenyl)piperazine (Method 27, 16 g, 68.027 mmol) and acetyl chloride (8.22 ml, 115.65 mmol) by the procedure of Method 26. It was obtained as a solid which was dried in vac oven overnight at 50° C. (20.5 g, 109%, contaminated with solvent). NMR (400 MHz) 1.19 (brd, 6H), 2.08 (s, 3H), 3.21 (brd, 2H), 4.00 (d, 2H), 4.34 (v brs, 2H), 7.08 (d, 2H), 8.06 (d, 2H); m/z 278.

Workup

  1. customIt was obtained as a solid which
  2. customwas dried in vac oven overnight at 50° C. (20.5 g, 109%, contaminated with solvent)

Sources & evidence

ORD record
ord-70417f3ed9154e4db7db3ca34625a155
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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