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

HRID 2088897Notes

Reaction equation

HRID 2088897 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[C:9]2[CH:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClCCl.Cl.O1CCOCC1>CO>[O:16]1[CH2:15][CH2:14][CH:13]([C:11]2[N:10]=[C:9]([CH:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)[N:8]([CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:12]=2)[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 67112170Tert-butyl 4-[1-(2-pyrrolidin-1-ylethyl)-4-tetrahydropyran-4-yl-imidazol-2-yl]piperidine-1-carboxylate

Product 1

HCID 671119654-(1-(2-pyrrolidin-1-yl-ethyl)-4-(tetrahydro-pyran-4-yl)-1H-imidazol-2-yl)-piperidineYield 124.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine tert-butyl 4-(1-(2-(pyrrolidin-1-yl)ethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate (1.74 g, 4.03 mmol), dichloromethane (53 mL) and methanol (21 mL). Add 4 M hydrogen chloride in 1,4-dioxane (10.4 mL, 10.3 eq). After one hour, concentrate in vacuo. Dry the resulting residue under vacuum to give the title compound as a white solid (1.67 g, 94%). MS (ES) m/z=333 [M]+.

Workup

  1. concentrationconcentrate in vacuo
  2. customDry the resulting residue under vacuum

Sources & evidence

ORD record
ord-6c13e202507649ec9900182ceae5bfa2
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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