Allyl bromide → Diallyl-thiophen-2-ylmethylamine

HRID 906637Notes

Reaction equation

HRID 906637 reaction equation
[NH2:1][CH2:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)[CH:11]([CH3:13])[CH3:12].[CH2:17](Br)[CH:18]=[CH2:19]>C(Cl)Cl>[CH2:13]([N:1]([CH2:19][CH:18]=[CH2:17])[CH2:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)[CH:11]=[CH2:12]

Participants

5

Reactant 3

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

Product 1

HCID 11159855Diallyl-thiophen-2-ylmethylamineYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-aminomethyl-thiophene (51.4 g, 956 mmol) and i-Pr2NEt (140 g, 1081 mmol) in CH2Cl2 (11) was placed in a 3-1 flask equipped with a condenser and an efficient magnetic agitation. Allyl bromide (115.7 g, 454 mmol) was added, whereupon the moderately exothermic reaction spontaneously reached the reflux temperature after 2 h. The mixture was stirred overnight (16 h), washed (NaHCO3 sat.; brine), dried (MgSO4), and concentrated. The resulting oil was filtered over silica gel (EtOAc:hexane 1:4). The filtrate was concentrated and the filtration was repeated to afford 70.3 g (80%) of the title diallylamine as a brown-yellow oil, clean by NMR: 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. customequipped with a condenser
  2. customafter 2 h
  3. washwashed (NaHCO3 sat.; brine)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. filtrationThe resulting oil was filtered over silica gel (EtOAc:hexane 1:4)
  7. concentrationThe filtrate was concentrated
  8. filtrationthe filtration

Sources & evidence

ORD record
ord-81568034d215442995610029dbbf6469
Source dataset
uspto-grants-2011_09
Patent number
US08012995B1

Reaction notes

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