Hydrochloric Acid → 4-(1-(2-pyrrolidin-1-yl-ethyl)-4-(tetrahydro-pyran-4-yl)-1H-imidazol-2-yl)-piperidine

HRID 2088923Notes

Reaction equation

Cl.[N:2]1([CH2:7][CH2:8][N:9]2[CH:13]=[C:12]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]2[CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)[CH2:6][CH2:5][CH2:4][CH2:3]1>C(O)(C)C>[O:17]1[CH2:16][CH2:15][CH:14]([C:12]2[N:11]=[C:10]([CH:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)[N:9]([CH2:8][CH2:7][N:2]3[CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:13]=2)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 50 °C

Procedure

Add aqueous 35% hydrochloric acid (23.20 mL, 4.7 eq) to a solution of tert-butyl 4-[1-(2-pyrrolidin-1-ylethyl)-4-tetrahydropyran-4-yl-imidazol-2-yl]piperidine-1-carboxylate (29.0 g, 60.33 mmol) in isopropyl alcohol (120 mL). Stir at 50° C. for six hours. Concentrate in vacuo. Add water (1 L) and 2 M aqueous sodium hydroxide to adjust the pH to 12. Extract with ethyl acetate (3×200 mL) and dichloromethane (3×200 mL). Dry the organics over anhydrous magnesium sulfate and concentrate in vacuo to give 4-(4-(tetrahydro-2H-pyran-4-yl)-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine (21.5 g, 100%). MS (ES) m/z=333 [M]+.

Workup

concentrationConcentrate in vacuo
extractionExtract with ethyl acetate (3×200 mL) and dichloromethane (3×200 mL)
dry with materialDry the organics over anhydrous magnesium sulfate
concentrationconcentrate in vacuo

Sources & evidence

ORD record: ord-3926288b4de044e081daf2262e84de18
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436002B2

Reaction notes

Loading…