Hydrochloric Acid → Ethyl 2-(4-Aminophenyl)-2-[isopropyl(methyl)amino]acetate

HRID 888443Notes

Reaction equation

HRID 888443 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([N:21]([CH:23]([CH3:25])[CH3:24])[CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=1)=O)(C)(C)C.Cl.O1CCOCC1>>[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([N:21]([CH:23]([CH3:24])[CH3:25])[CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57625158Ethyl 2-[4-(tert-Butoxycarbonylamino)phenyl]-2-[isopropyl(methyl)amino]acetate

Product 1

HCID 57625093Ethyl 2-(4-Aminophenyl)-2-[isopropyl(methyl)amino]acetateYield 81%

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 26 (1.19 g, 3.40 mmol) and 4M hydrogen chloride in 1,4-dioxane (15.0 mL, 60 mmol), and the mixture was stirred at room temperature for 4 h. After this time, the reaction mixture was concentrated under reduced pressure, and the resulting residue was partitioned between 10% aqueous potassium carbonate (100 mL) and methylene chloride (75 mL). The layers were separated, and the aqueous phase was extracted with methylene chloride (2×75 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 27 in 81% yield (878 mg) as an orange solid: mp 70-71° C.; 1H NMR (500 MHz, DMSO-d6) δ 7.02 (d, 2H, J=7.5 Hz), 6.49 (d, 2H, J=7.5 Hz), 5.07 (bs, 2H), 4.07-3.97 (m, 3H), 2.81 (septet, 1H, J=6.5 Hz), 1.99 (s, 3H), 1.11 (t, 3H, J=7.0 Hz), 0.92 (d, 3H, J=6.5 Hz), 0.85 (d, 3H, J=6.5 Hz); MS (ESI+) m/z 251 (M+H).

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was partitioned between 10% aqueous potassium carbonate (100 mL) and methylene chloride (75 mL)
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with methylene chloride (2×75 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5e6be4795f84d14b1ee4289a073cc7c
Source dataset
uspto-grants-2012_08
Patent number
US08247550B2

Reaction notes

Loading…