Methyl iodide → 4-Benzyloxycarbonyl-1-{methyl[1-(tert-butoxycarbonyl)-4-piperidinyl]amino}-2-piperazinone

HRID 2086236Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[C:13](=[O:31])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([N:17]([CH3:32])[CH:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:22][CH2:23]2)[C:13](=[O:31])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-benzyloxycarbonyl-1-[1-(tert-butoxycarbonyl)-4-piperidinylamino]-2-piperazinone (9.00 g), potassium carbonate (3.46 g) and methyl iodide (29.81 g) in DMF (100 ml) was stirred at 50° C. overnight. The reaction mixture was concentrated under reduced pressure, and the residue was combined with water (200 ml) and extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1, 120 ml×3). The extract was washed with water and brine, dried and concentrated. The residue was crystallized from diisopropyl ether to obtain the title compound (8.55 g) as colorless crystals.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with a mixture of ethyl acetate and tetrahydrofuran (1:1, 120 ml×3)
washThe extract was washed with water and brine
customdried
concentrationconcentrated
customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record: ord-710de33dfc4145ba9f30b16917b1a8f7
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723722B1

Reaction notes

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