Methyl 2-(4-benzyl-1-(4-methyl-2-nitrophenyl)piperazin-2-yl)acetate → 3-Benzyl-9-methyl-1,2,3,4,4a,5-hexahydropyrazino[1,2-a][1,5]benzodiazepin-6(7h)-one

HRID 80512Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[N+:21]([O-])=O)[CH:10]([CH2:24][C:25]([O:27]C)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Fe]>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=3[NH:21][C:25](=[O:27])[CH2:24][CH:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of Example 49A (150 mg, 0.392 mmol) in acetic acid (5 mL) was added iron powder (65.5 mg, 1.17 mmol), and the reaction was heated to 80° C. for 14 hours. The solution was then concentrated onto silica gel and purified via flash chromatography (0-30% methanol/dichloromethane). The pure fractions were partitioned between dichloromethane and 1M NaOH. The organic layer was collected and dried with MgSO4 to afford title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.41 (s, 1H), 7.20-7.41 (m, 5H) 6.86-7.01 (m, 2H), 6.73 (s, 1H), 3.53 (s, 2H), 3.02-3.27 (m, 2H), 2.67-3.00 (m, 3H), 2.42-2.48 (m, 1H) 2.04-2.30 (m, 5H) 1.84 (d, J=13.22 Hz, 1H); MS (APCI+) m/z 322 (M+H)+.

Workup

concentrationThe solution was then concentrated onto silica gel
custompurified via flash chromatography (0-30% methanol/dichloromethane)
customThe pure fractions were partitioned between dichloromethane and 1M NaOH
customThe organic layer was collected
dry with materialdried with MgSO4

Sources & evidence

ORD record: ord-a7a51c5d7b8c47c6a4aca84f5ffefbd4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846663B2

Reaction notes

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