Methanol → HCID 58193756, compound

3.6 g (31.5 mmol) of 1 was mixed with 100 mL of methanol, followed by adding triethyl amine to adjust pH to 9-10 to obtain a first reaction solution. 5.1 g (28.7 mmol) of 2 was mixed with 100 mL of methanol to obtain a second reaction solution. The second reaction solution was added dropwisely into the first reaction solution to obtain a reaction mixture. The reaction mixture was subjected to reflux reaction at 60-70° C. for 19 hours, followed by evaporation to obtain a crude product. The crude product was dissolved in ammonia, followed by extracting with chloroform and water and evaporating to obtain a product of 2.9 g (11.1 mmol, 38.6%) of a light-yellow oil 3. The analytic data of the product are as follows: 1H-NMR (D2O, 400 MHz), δ(ppm): 7.29-7.15 (m, 5H, Ar), 3.57 (t, 1H, J=3, H2NCH), 3.20-2.95 (m, 2H, NHCH2), 2.89-2.76 (m, 2H, CH2Ar), 2.21-2.05 (m, CH2NH2), 1.69-1.66 (m, 2H, CH2CH2CH2), 1.52-1.45 (m, 4H, CH2CH2CH2); 13C-NMR (D2O, 100 MHz), δ(ppm): 176.88, 137.37, 129.38, 128.90, 127.11, 56.60, 45.82, 43.99, 42.36, 40.90, 26.59, 26.51, 14.27; ESI-MS (m/z): calcd. 261.36, found 262.18 [M+H]+; Anal. Calcd (Found) for C15H23N3O.HCl: C, 60.94 (60.49); H, 8.43 (8.12); N, 14.53 (14.11).

1. customto obtain a first reaction solution
2. customto obtain a second reaction solution
3. additionThe second reaction solution was added dropwisely into the first reaction solution
4. customto obtain a reaction mixture
5. temperatureto reflux
6. customreaction at 60-70° C. for 19 hours
7. customfollowed by evaporation
8. customto obtain a crude product
9. extractionby extracting with chloroform and water
10. customevaporating

ORD record

ord-de25b230de5c44128ac6391c57789d4b

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354512B2