Formaldehyde → 6-Ethoxy-1,2,3,4-tetrahydroisoquinoline

温度

110 °C

A stirred mixture of 2-(3-ethoxy-phenyl)-ethylamine (7.0 g, 42 mmol) and 37% aqueous formaldehyde solution (3.5 mL) was heated at 110° C. for 30 minutes. The stirring was stopped and the upper water layer was removed by pipette. To the resulting mixture water (5.25 mL) and concentrated HCl (10.5 mL) were added followed by heating 100° C. for 30 minutes. After allowing to cool to room temperature the mixture was evaporated to dryness and recrystallised from acetone yielding the subtitled compound as a cream solid (2.73 g). MH+ 178. 1H NMR δ (DMSO) 1.27-1.35 (3H, t), 2.88-3.03 (2H, t), 3.18-3.40 (2H, br, t), 3.95-4.08 (2H, q), 4.10-4.22 (2H, m), 6.74-6.85 (2H, m), 7.05-7.15 (1H, m), 9.33-9.55 (2H, br.s).

1. customthe upper water layer was removed by pipette
2. additionTo the resulting mixture water (5.25 mL) and concentrated HCl (10.5 mL) were added
3. temperatureby heating 100° C. for 30 minutes
4. temperatureto cool to room temperature the mixture
5. customwas evaporated to dryness
6. customrecrystallised from acetone yielding the subtitled compound as a cream solid (2.73 g)

ORDレコード

ord-b0f73e038fb84aee8e0beadb0311b188

出典データセット

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07504392B2