Pyridine → HCID 20144171, compound
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][CH2:11]O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[N:24]1C=CC=C[CH:25]=1>>[CH3:25][NH:24][CH2:11][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1Participants
Procedure
A solution of 5.03 g of 3-benzofuranethanol and 8 g of p-toluenesulfonyl chloride in 20 ml of pyridine was kept in a refrigerator for one week. Most of the pyridine was removed under vacuum, and the residue dissolved in ether and washed successively with 5% hydrochloric acid, water, and 5% sodium bicarbonate solution and dried. Removal of the solvent left 5.93 g of crude 3-benzofuranethanol, p-toluenesulfonate which was heated with 8 g of methylamine in 25 ml of tetrahydrofuran to 100° for 4 hours. The mixture was concentrated, made basic with aqueous sodium hydroxide, and extracted with methylene chloride. The crude amine so obtained was short-path distilled (bath 120°, 0.5 micron) to give 3.17 g (59% yield) of N-methyl 3-benzofuranethylamine. NMR spectrum (in CDCl3): τ2.4-3.0 (m, 5); 7.2 (s, 4); 7.6 (s, 3) and 9.0 (s, 1).
Workup
- customMost of the pyridine was removed under vacuum
- dissolutionthe residue dissolved in ether
- washwashed successively with 5% hydrochloric acid, water, and 5% sodium bicarbonate solution
- customdried
- customRemoval of the solvent
- waitleft 5.93 g of crude 3-benzofuranethanol, p-toluenesulfonate which
- temperaturewas heated with 8 g of methylamine in 25 ml of tetrahydrofuran to 100° for 4 hours
- concentrationThe mixture was concentrated
- extractionextracted with methylene chloride
- customThe crude amine so obtained
- distillationwas short-path distilled (bath 120°, 0.5 micron)
Sources & evidence
- ORD record
- ord-0b8c4f316ce546c096516ccea70d2df5
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04243668
Reaction notes
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