p-Toluenesulfonic acid → Allyl-(1-methyl-pent-4-enylidene)-amine Allyl-(1-methyl-pent-4-enyl)-amine

HRID 1790607Notes

Reaction equation

HRID 1790607 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][CH:5]=[CH2:6].[CH2:8]([NH2:11])[CH:9]=[CH2:10].[C:12]1(C)[CH:17]=[CH:16][C:15](S(O)(=O)=O)=[CH:14][CH:13]=1>C(Cl)Cl>[CH2:8]([NH:11][CH:2]([CH3:1])[CH2:3][CH2:4][CH:5]=[CH2:6])[CH:9]=[CH2:10].[CH2:8]([N:11]=[C:16]([CH3:15])[CH2:17][CH2:12][CH:13]=[CH2:14])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7853AllylamineHCID 79895-Hexene-2-one

Product 1

HCID 22036684Allyl-(1-methyl-pent-4-enylidene)-amine Allyl-(1-methyl-pent-4-enyl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hex-5-en-2-one (9.8 g, 11.6 ml, 100 mmol) was added to a stirred solution of allylamine (8.55 mmol, 11.25 ml, 150 mmol), 4 Angstrom molecular sieves (52 g), and p-toluene sulfonic acid (10 mg) in CH2Cl2 (200 ml) and was stirred overnight. The reaction mixture was concentrated in vacuo by rotary evaporation and was used in the next reaction without further purification (13 g, 95%). Electrospray mass spec: M+H+=137.9

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo by rotary evaporation
  2. customwas used in the next reaction without further purification (13 g, 95%)

Sources & evidence

ORD record
ord-09f4020875874426a74d475a4e4e5dbd
Source dataset
uspto-grants-2006_07
Patent number
US07071184B2

Reaction notes

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