Benzene → N-Methyl-N-[4-(1-methyl-1-phenylethyl)benzyl]-(3-isopropenylbenzyl)amine

HRID 1356847Notes

Reaction equation

HRID 1356847 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:12][C:13]([CH3:31])([CH3:30])[C:14]#[C:15]/[CH:16]=[CH:17]/[CH2:18][N:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25](F)=[C:24](Br)[CH:23]=1)[CH3:20].[CH:32]1C=CC=C[CH:33]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:20][N:19]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:2]([CH3:1])=[CH2:3])[CH:23]=1)[CH2:18][C:17]1[CH:33]=[CH:32][C:14]([C:13]([CH3:31])([C:30]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH3:12])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 241Benzene2×HCID 8058HexaneHCID 18509463trans-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-(3-bromo-4-fluorobenzyl)amineHCID 178418339Butyllithium

Product 1

HCID 18509461N-Methyl-N-[4-(1-methyl-1-phenylethyl)benzyl]-(3-isopropenylbenzyl)amine

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

Methyl triphenyl phosphonium bromide (1.67 g; 4.68 mmol) was added to benzene (20 ml). While the mixture was stirred under nitrogen atmosphere at room temperature, n-butyl lithium in n-hexane (1.63 M: 2.9 ml; 4.73 mmol) was added dropwise. The mixture was stirred for 5 minutes, and Compound 28 (1.16 g; 3.12 mmol) in benzene (5 ml) was added dropwise thereto, followed by stirring overnight at room temperature. Reaction was stopped by pouring the mixture into ice/water, followed by extraction with benzene (100 ml).

Workup

  1. stirringThe mixture was stirred for 5 minutes
  2. stirringby stirring overnight at room temperature
  3. customReaction
  4. extractionfollowed by extraction with benzene (100 ml)

Sources & evidence

ORD record
ord-8e60c00351554a89965fccaf63c77770
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

Loading…