Hydrochloric Acid → (S)-1-acetyl-2-methyl-4-nitrosopiperazine

HRID 1596209Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][C@@H:5]1[CH3:10])(=[O:3])[CH3:2].Cl.[N:12]([O-])=[O:13].[Na+].[OH-].[Na+]>O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([N:12]=[O:13])[CH2:6][C@@H:5]1[CH3:10])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a slurry of (S)-1-acetyl-2-methylpiperazine (424 mg) in water (2.5 ml) was added concentrated hydrochloric acid (0.9 ml) dropwise below 25° C. A solution of sodium nitrite (227 mg) in water (2 ml) was added dropwise at 0° C. The mixture was stirred at 0° C. for 2 hours. A solution of sodium hydroxide (409 mg) in water (6 ml) was added dropwise at 0° C. The mixture was extracted with chloroform, washed with water, dried and evaporated to give (S)-1-acetyl-2-methyl-4-nitrosopiperazine (350 mg). This product was used for next step without purification.

Workup

extractionThe mixture was extracted with chloroform
washwashed with water
customdried
customevaporated

Sources & evidence

ORD record: ord-2db1d6d7dcb8418f837c126d3bcfd1db
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291464B1

Reaction notes

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