Nitrogen → HCID 89813373, compound

HRID 715112Notes

Reaction equation

[H-].[K+].N#N.[CH2:5]([N:12]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:13][CH2:14][C:15]([CH3:18])([OH:17])[CH3:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:26]I.[NH4+].[Cl-]>C1COCC1>[CH2:19]([N:12]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:13][CH2:14][C:15]([O:17][CH3:26])([CH3:18])[CH3:16])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Add potassium hydride (30%, 2.6 g, 19.4 mmol) portion wise under N2 to a 0° C. solution of 4-(dibenzylamino)-2-methylbutan-2-ol (5 g, 17.6 mmol) in THF (50 mL). Stir the mixture at 0° C. for 0.5 h, treat drop-wise with methyl iodide [MeI] (2.76 g, 19.4 mmol), allow the mixture to warm to RT and stir for 3 h. Re-cool the mixture to 0° C., treat with saturated NH4Cl, and remove the organics under reduced pressure. Extract the residue with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate and purify via silica gel chromatography (Pet ether/EtOAc, 50:1) to afford the title compound (3.0 g, 57%). 1H NMR (400 MHz, DMSO-d6): δ 7.29 (m, 10H), 3.58 (s, 4H), 3.05 (s, 3H), 2.50 (m, 2H), 1.73 (m, 2H), 1.07 (s, 6H).

Workup

additiontreat
temperatureto warm to RT
stirringstir for 3 h
customremove the organics under reduced pressure
extractionExtract the residue with EtOAc (3×)
washwash the combined organics with brine
dry with materialdry over Na2SO4
concentrationconcentrate
custompurify via silica gel chromatography (Pet ether/EtOAc, 50:1)

Sources & evidence

ORD record: ord-18fb71a43e1c4eeaba5495114274095d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187474B2

Reaction notes

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