Hydrochloric Acid → HCID 66877304, compound

HRID 1993872Notes

Reaction equation

HRID 1993872 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([N:13]2[C:17]3[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=3[N:15]=[C:14]2[CH3:23])[CH2:9]1)(C)(C)C.CO.[ClH:27]>O1CCOCC1>[ClH:27].[CH3:23][C:14]1[N:13]([C@H:10]2[CH2:11][CH2:12][C@H:8]([NH2:7])[CH2:9]2)[C:17]2[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:16]=2[N:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66877180trans-[3-(2,5-Dimethyl-benzoimidazol-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester

Product 1

HCID 66877304HCID 66877304, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The trans-[3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester prepared above (320 mg, 0.95 mmol) was dissolved in HCl (4M) in dioxane (5.0 mL) and the solution was stirred for 15 minutes. Solids came out of solution and 1 mL of methanol was added to dissolve the precipitate. Stirring was continued for 60 minutes and the reaction mixture was evaporated to a sticky solid which was stirred with ethyl ether. The resulting solid was filtered to provide trans-3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentylamine hydrochloride salt as an off white powder (250 mg). LR-MS calcd for C14H19N3 (m/e) 229.1579, obsd 230.2 (M+H).

Workup

  1. additionwas added
  2. dissolutionto dissolve the precipitate
  3. stirringStirring
  4. waitwas continued for 60 minutes
  5. customthe reaction mixture was evaporated to a sticky solid which
  6. stirringwas stirred with ethyl ether
  7. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-40d13ccc93ed474096ae4f646685e45f
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

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