Ethanol → methyl(2-(1H-pyrrol-1-yl)ethyl)amine

HRID 1405339Notes

Reaction equation

HRID 1405339 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1.[CH3:9][NH2:10].C(O)C>>[CH3:9][NH:10][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 126741701-(2-Chloroethyl)pyrrole

Product 1

HCID 59730499methyl(2-(1H-pyrrol-1-yl)ethyl)amineYield 88%

Conditions

Temperature
90 °C

Procedure

1-(2-Chloroethyl)pyrrole (2.0 g, 15.43 mmol) was combined with a solution of 33% methylamine in ethanol (7.3 mL of 33% w/v, 77.15 mmol). The mixture was heated at 90° C. for 16 h before it was concentrated under reduced pressure to provide N-methyl-2-pyrrol-1-yl-ethanamine (2.19 g, 88%) which was used directly in next reaction. ESI-MS m/z calc. 124.1, found 125.3 (M+1)+; Retention time: 0.22 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 6.73-6.68 (m, 2H), 6.22-6.14 (m, 2H), 4.05 (t, J=5.9 Hz, 2H), 2.94 (t, J=5.9 Hz, 2H), 2.45 (s, 3H).

Workup

  1. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-14b425c4af3e44a39d5f9a74c5197a93
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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