1-Acetylpiperazine → HCID 86690653, compound

HRID 1505620Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([C:20]([CH3:23])([CH3:22])[CH3:21])[S:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:4][CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC(C)C)=CC=CC=2OC(C)C)CCCCC1.[N:57]1([C:63](=[O:65])[CH3:64])[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[C:63]([N:57]1[CH2:62][CH2:61][N:60]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][N:9]([C:20]([CH3:23])([CH3:22])[CH3:21])[S:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:12])=[O:11])=[CH:4][CH:3]=2)[CH2:59][CH2:58]1)(=[O:65])[CH3:64]

Participants

Conditions

Temperature: 100 °C

Procedure

In a vial, N-[(4-bromophenyl)methyl]-N-tert-butyl-1-phenylmethanesulfonamide (186 mg; 0.47 mmol), palladium(II) acetate (5 mg, 0.023 mmol), 2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl (22 mg, 0.047 mmol) sodium tert-butoxide (61 mg, 0.61 mmol) were weighed out and the vial was purged with nitrogen. 1,4-Dioxane (3 mL) and 1-piperazin-1-ylethanone (78 mg, 0.61 mmol) were then added and the reaction was stirred at 100° C. for 16 hours. The reaction was filtered through diatomaceous earth, concentrated and purified by preparative reverse phase HPLC to yield 141 mg of N-(4-(4-acetylpiperazin-1-yl)benzyl)-N-tert-butyl-1-phenylmethanesulfonamide. 1H NMR (400 MHz, DMSO) δ 7.47-7.33 (m, 5H), 7.27-7.16 (m, 2H), 6.96-6.83 (m, 2H), 4.41 (s, 2H), 4.16 (s, 2H), 3.62-3.49 (m, 4H), 3.19-3.09 (m, 2H), 3.09-2.95 (m, 2H), 2.03 (s, 3H), 1.33 (s, 9H); LCMS (m/z) ES+ 444.1 [M+1]+.

Workup

customthe vial was purged with nitrogen
filtrationThe reaction was filtered through diatomaceous earth
concentrationconcentrated
custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-1475a33dc018478c822ff24414b0f1d5
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216988B2

Reaction notes

Loading…