Ethyl Acetate → HCID 23441060, compound

HRID 2119363Notes

Reaction equation

Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C([O-])([O-])=O.[K+].[K+].[C:18]([O:22][C:23]([N:25]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].CCOC(C)=O>CC#N>[C:18]([O:22][C:23]([N:25]1[CH2:31][CH2:30][CH2:29][N:28]([CH2:2][CH2:3][C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 70 °C

Procedure

3-Chloropropiophenone (7.14 g, 24.4 mmol). K2CO3 (8.79 g, 1.50 equiv) and KI (1.41 mg, 0.2 equiv) were added to a solution of the purified 1-(tert-butyloxycarbonyl)homopiperazine (8.486 g, 42.4 mmol) in CH3CN (60 mL). The reaction mixture was stirred at 70° C. for 17 h and then AcOEt (200 mL) was added to the cooled mixture. The precipitated solid was removed by filtration and washed with AcOEt (50 mL). The combined filtrate was evaporated to afford an oil which was purified by column chromatography (SiO2, 0%-20% CH3CN/AcOEt) to give 1-(tert-Butyloxycarbonyl)-4-(3-phenyl-3-oxopropyl)homopiperazine: 11.27 g, 80% yield, pale yellow oil: 1H NMR (CDCl3, 300 MHz) δ 1.40-1.65 (m, 9H), 1.80-1.95 (m, 2H), 2.65-2.85 (m, 4H), 3.01 (t, 2H, J=6.9 Hz), 3.19 (t, 2H, J=6.9 Hz), 3.35-3.55 (m, 4H), 7.47 (t, 2H, J=7.7 Hz), 7.55-7.65 (m, 1H), 7.90-8.02 (m, 2H). The purity was determined by RPLC/MS (Method B). RPLC tR=5.53 min (95%), 220 nm; ESI/MS m/e 333.4 (M++H, C19H29N2O3).

Workup

customThe precipitated solid was removed by filtration
washwashed with AcOEt (50 mL)
customThe combined filtrate was evaporated
customto afford an oil which
customwas purified by column chromatography (SiO2, 0%-20% CH3CN/AcOEt)

Sources & evidence

ORD record: ord-88fefcbeeb654892845b4216002e34c8
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06686353B1

Reaction notes

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