Hydrochloric Acid → Hydrochloric Acid

HRID 2361710Notes

Reaction equation

HRID 2361710 reaction equation
[I:1][CH:2]1[CH2:10][CH:9]2[CH2:11][C:5]3([NH:13]C(=O)OC(C)(C)C)[CH2:6][CH:7]([CH2:12][CH:3]1[CH2:4]3)[CH2:8]2.[ClH:21]>O1CCOCC1>[ClH:21].[I:1][CH:2]1[CH2:10][CH:9]2[CH2:11][C:5]3([NH2:13])[CH2:6][CH:7]([CH2:12][CH:3]1[CH2:4]3)[CH2:8]2.[ClH:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86673700HCID 86673700, compound

Product 2

HCID 313Hydrochloric AcidHCID 78079163HCID 78079163, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of carbamate 5A (0.10 mmol) in 1,4-dioxane (2 mL) was added a solution of 4 N HCl in dioxane (1.0 mL) and the mixture was maintained at rt for 16 h. The reaction mixture was concentrated and the residue was dissolved in water (2 mL). The aqueous layer was washed with EtOAc (3×5 mL) and concentrated to provide amine (5) in 64% yield as a hydrochloric acid salt. Data: LC/MS (ESR) m/z 292 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water (2 mL)
  3. washThe aqueous layer was washed with EtOAc (3×5 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-67c533c2597a4a0aae7992ee2b73eeb7
Source dataset
uspto-grants-2014_04
Patent number
US08691808B2

Reaction notes

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