Methyl iodide → N,N-dibenzyl-2-(1-methoxycyclopropyl)ethanamine

HRID 2278943Notes

Reaction equation

[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH2:10][C:11]1([OH:14])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I>C1COCC1>[CH2:15]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH2:10][C:11]1([O:14][CH3:24])[CH2:12][CH2:13]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 0° C. solution of 1-(2-(dibenzylamino)ethyl)cyclopropanol (3 g, 10.6 mmol) in THF (50 mL), under N2, was treated portion-wise with NaH (60%, 0.85 g, 21.3 mmol), stirred at 0° C. for 0.5 h, treated drop-wise with MeI (1.82 g, 12.8 mmol), warmed to RT and stirred for 3 h. The mixture was cooled to 0° C., quenched with satd. NH4Cl and partially concentrated. The residue was extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4, concentrated and purified via silica gel chromatography to afford N,N-dibenzyl-2-(1-methoxycyclopropyl)ethanamine (1.2 g, 38%). 1H NMR (400 MHz, CDCl3): δ 7.39-7.21 (m, 10 H), 3.60 (s, 4 H), 3.12 (s, 3 H), 2.65 (t, J=8 Hz, 2 H), 1.75 (t, J=8 Hz, 2 H), 0.68-0.65 (m, 2 H), 0.34-0.31 (m, 2 H).

Workup

temperaturewarmed to RT
stirringstirred for 3 h
temperatureThe mixture was cooled to 0° C.
customquenched with satd
concentrationNH4Cl and partially concentrated
extractionThe residue was extracted with EtOAc (3×)
washthe combined organics were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
custompurified via silica gel chromatography

Sources & evidence

ORD record: ord-859d322bca53416e81367c6383f6823a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133183B2

Reaction notes

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