Hexane → N-Cinnamyl-N-methyl-(3-isopropenylbenzyl)amine

HRID 1356825Notes

Reaction equation

HRID 1356825 reaction equation
[CH2:1]([N:10]([CH2:12][C:13]1[CH:14]=[C:15]([C:19](=O)[CH3:20])[CH:16]=[CH:17][CH:18]=1)[CH3:11])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:22]([Li])CCC.CCCCCC>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([CH3:20])=[CH2:22])[CH:14]=1)[CH3:11])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 699361453'-(N-Cinnamyl-N-methylaminomethyl)acetophenoneHCID 178418339Butyllithium

Product 1

HCID 69933763N-Cinnamyl-N-methyl-(3-isopropenylbenzyl)amineYield 50.5%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

The procedure described in Example 2 was repeated, except that Compound 46 (0.42 g; 1.50 mmol), methyl triphenylphosphonium bromide (1.5 eq), and n-butyl lithium in n-hexane (1.68 M: 1.5 eq) were used, to thereby yield 0.21 g of the target compound (yield: 50.5%).

Sources & evidence

ORD record
ord-43b7370eaf3c4c33b1fc42b9c3b5417d
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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