N-Methylbenzylamine → HCID 57925932, compound

HRID 1013502Notes

Reaction equation

[CH:1]([P:4](=[O:10])([CH:7]([CH3:9])[CH3:8])[CH:5]=[CH2:6])([CH3:3])[CH3:2].[CH3:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([N:12]([CH3:11])[CH2:6][CH2:5][P:4]([CH:7]([CH3:9])[CH3:8])([CH:1]([CH3:3])[CH3:2])=[O:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Reactant 2

HCID 7669N-Methylbenzylamine

HCID 57925973HCID 57925973, compound

Product 1

HCID 57925932HCID 57925932, compound

Conditions

Temperature: 200 °C

Procedure

Diisopropyl(vinyl)phosphine oxide (1.00 g, 6.24 mmol) was combined with N-methylbenzylamine (1.61 mL, 12.48 mmol) in a microwave vial and heated at 200° C. for 4 h total (reaction progress checked after 2 h). The crude mixture was directly purified by flash chromatography (0-10% MeOH/CH2Cl2). Coelution of the product with minor impurities required a second column (0-10% MeOH (w/2 N NH3)/CH2Cl2) to give clean product as a yellow oil. 1H NMR (CDCl3, 600 MHz) δ 7.30-7.20 (m, 5H), 3.50 (s, 2H), 2.76-2.70 (m, 2H), 2.20 (s, 3H), 2.00-1.92 (m, 2H), 1.90-1.84 (m, 2H), 1.17 (dd, J=14.6, 7.2 Hz, 6H), 1.12 (dd, J=15.1, 7.1 Hz, 6H). MS: cal'd 282 (MH+), exp 282 (MH+).

Workup

customtotal (reaction progress checked after 2 h)
customThe crude mixture was directly purified by flash chromatography (0-10% MeOH/CH2Cl2)
customto give clean product as a yellow oil

Sources & evidence

ORD record: ord-df379d8d4e6c493381de30854acbf086
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981874B2

Reaction notes

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