Hydrochloric Acid → 5-[(2R)-2-amino-2-phenylethoxy]-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

HRID 1038975Notes

Reaction equation

HRID 1038975 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][C@H:13]([NH:20]C(=O)OC(C)(C)C)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][C:4]=2[NH:3]1.[ClH:28]>C1COCC1>[ClH:28].[NH2:20][C@H:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2](=[O:1])[NH:3][C:4]=2[CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68240928tert-Butyl{(1R)-2-[(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)oxy]-1-phenylethyl}carbamate2×

Product 1

HCID 673985985-[(2R)-2-amino-2-phenylethoxy]-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl {(1R)-2-[(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)oxy]-1-phenylethyl}carbamate (Intermediate 7) (67 mg, 0.18 mmol) was placed in a 10-mL RBF under a nitrogen atmosphere and dissolved in THF (2 mL). HCl (1 mL, 4.0 mmol) (4M in 1,4-dioxane) was added, and the reaction was stirred at room temperature for sixteen hours. The reaction then concentrated in vacuo, with repeated cycles of dilution/concentration with THF to minimize the residual HCl, to afford 5-[(2R)-2-amino-2-phenylethoxy]-1,3-dihydro-2H-benzimidazol-2-one hydrochloride as a yellow solid. LRMS (ESI) calc'd for (C15H16N3O2) [M+H]+, 270.1. found 270.1.

Workup

  1. customThe reaction
  2. concentrationthen concentrated in vacuo
  3. concentrationcycles of dilution/concentration with THF

Sources & evidence

ORD record
ord-e5686bd74e464e53bed156b2b00211c8
Source dataset
uspto-grants-2013_10
Patent number
US08552019B2

Reaction notes

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