Sodium Hydroxide → HCID 14969511, compound

A solution of methyl 3-(2-(1-methylpiperidin-4-ylamino)phenyl)propanoate (1.1 g, 3.98 mmol) in 20 mL MeOH/5 mL H2O was treated with 1N NaOH (8.8 mL, 8.76 mmol) and stirred at room temperature for 2 hours. The mixture was concentrated and made acidic with 6N HCl. Approximately half of this mixture was diluted with 1N HCl (15 mL) and heated at 110° C. overnight. After cooling, the mixture was concentrated on the rotoevaporator then made basic with saturated Na2CO3. This solution was extracted with 2×100 mL CH2Cl2. The combined organic fractions were dried over MgSO4, filtered and concentrated to give a light brown residue, which was subjected to flash chromatography on silica gel using 5%, 2M NH3 in MeOH/CH2Cl2. A light yellow solid was obtained (320 mg, 78.2%). 1H-NMR (CDCl3) δ 7.24-7.16 (m, 3H), 7.02-6.97 (m, 1H), 4.47-4.34 (m, 1H), 2.99-2.95 (m, 2H), 2.83-2.70 (m, 2H), 2.68-2.55 (m, 4H), 2.33 (s, 3H), 2.13-2.06 (m, 2H), 1.72-1.69 (m, 2H). MS (ESI): 245.2 (M+1, 100%).

1. concentrationThe mixture was concentrated
2. additionApproximately half of this mixture was diluted with 1N HCl (15 mL)
3. temperatureheated at 110° C. overnight
4. temperatureAfter cooling
5. concentrationthe mixture was concentrated on the rotoevaporator
6. extractionThis solution was extracted with 2×100 mL CH2Cl2
7. dry with materialThe combined organic fractions were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a light brown residue, which
11. customA light yellow solid was obtained (320 mg, 78.2%)

ORD record

ord-41963f2970cd40388071029e66f8bc2d

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173813B2