Allyl bromide → Diallyl-thiophen-2-ylmethylamine

HRID 1869268Notes

Reaction equation

HRID 1869268 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[NH2:5][CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.CCN(C(C)C)[CH:15]([CH3:17])[CH3:16]>C(Cl)Cl>[CH2:1]([N:5]([CH2:17][CH:15]=[CH2:16])[CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 34005(2-Thienylmethyl)amineHCID 81531Diisopropylethylamine

Product 1

HCID 11159855Diallyl-thiophen-2-ylmethylamineYield 801.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Allyl bromide (55 ml, 65.4 mmol) is added to a solution of 2-aminomethyl-thiophene (24 ml, 23.3 mmole) and i-Pr2NEt (120 ml, 70.1 mmol) in CH2Cl2 (270 ml). The moderately exothermic reaction spontaneously reaches the reflux temperature after 1 h. The reaction is cooled by means of an ice bath and stirred for 14 h at rt. whereupon an undesired precipitate appeared. This precipitate (45 g) is removed by filtration. The organic layer is evaporated and diluted with EtOAc, whereupon more precipitate appears (45 g), which is removed by filtration. The EtOAc solution is filtered over SiO2 and concentrated to give 36.1 g (80%) of the title diallylamine as a pale yellow oil: 1H NMR (CDCl3) δ 7.25 (br. d, J=5.9 Hz, 1H), 6.98 (br. dd, J=5.1, 2.8 Hz, 1H), 6.94-6.92 (m, 1H), 5.99-5.86 (m, 2H), 5.29-5.18 (m, 4H), 3.85 (s, 2H), 3.16 (dd, J=6.3, 0.9 Hz, 4H).

Workup

  1. customThe moderately exothermic reaction
  2. customafter 1 h
  3. temperatureThe reaction is cooled by means of an ice bath
  4. customThis precipitate (45 g) is removed by filtration
  5. customThe organic layer is evaporated
  6. additiondiluted with EtOAc
  7. customis removed by filtration
  8. filtrationThe EtOAc solution is filtered over SiO2
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e475d8a029184c7e974ba1d9704dc9ca
Source dataset
uspto-grants-2009_12
Patent number
US07638538B1

Reaction notes

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