Dibenzylamine → N,N-Dibenzyl-2-methyl-5-decyn-4-amine

HRID 1711987Notes

Reaction equation

[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:7][CH:8]([CH3:12])[CH2:9][CH:10]=O.[CH2:13]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Cu]Br>[CH2:21]([N:20]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:10]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:9][CH:8]([CH3:12])[CH3:7])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A 10 ml schlenk tube was charged with copper (I) bromide (3.6 mg, 0.025 mmol), (R,Sax)-[4-(2-diphenylphosphanylnaphthalen-1-yl)-phthalazin-1-yl]-(1-phenylethyl)-amine (15.4 mg, 0.028 mmol) and 4 Å molecular sieves (0.3 g). The schlenk tube was flushed with argon for 5 min and then toluene (2 ml) was added. The resulting suspension was stirred for 1 hr at 23° C. To the reaction mixture was subsequently added 1-hexyne (41 mg, 0.50 mmol), 3-methylbutanal (43 mg, 0.50 mmol) and dibenzylamine (99 mg, 0.50 mmol). The resulting reaction mixture was stirred at 23° C. for 5 days and purified by flash chromatography on silica gel to give 128 mg of the title compound as a colorless oil.

Workup

customThe schlenk tube was flushed with argon for 5 min
additiontoluene (2 ml) was added
customThe resulting reaction mixture
stirringwas stirred at 23° C. for 5 days
custompurified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-30226b52146349f6ae284d83bc0519ab
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790882B2

Reaction notes

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