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

HRID 2088914Notes

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>[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[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

Add 5 M hydrogen chloride in isopropyl alcohol (112.7 mL, 5.0 eq) to a solution of tert-butyl 4-(1-(2-(pyrrolidin-1-yl)ethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate (132.0 g, 274.61 mmol) in isopropyl alcohol (549 mL). Stir the reaction mixture at 50° C. for six hours. Concentrate in vacuo. Dilute with water (1 L) and adjust the pH to 12 with 2 M aqueous sodium hydroxide. Extract with ethyl acetate and dichloromethane. Dry the organics over anhydrous magnesium sulfate and concentrate in vacuo to give 4-(1-(2-pyrrolidin-1-yl-ethyl)-4-(tetrahydro-pyran-4-yl)-1H-imidazol-2-yl)-piperidine (81.9 g, 90%). MS (ES) m/z=333 [M]+.

Workup

concentrationConcentrate in vacuo
additionDilute with water (1 L)
extractionExtract with ethyl acetate and dichloromethane
dry with materialDry the organics over anhydrous magnesium sulfate
concentrationconcentrate in vacuo

Sources & evidence

ORD record: ord-1d2efc162a98420688630761c1829d13
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436002B2

Reaction notes

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