Hydrochloric Acid → HCID 86711839, compound

HRID 623754Notes

Reaction equation

HRID 623754 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:11][C:12]([CH3:20])([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[CH3:13])C(=O)OC(C)(C)C>O1CCOCC1.CCOCC>[ClH:1].[CH3:2][NH:3][CH2:11][C:12]([CH3:20])([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)[CH3:13]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86711838HCID 86711838, compound

Product 1

HCID 86711839HCID 86711839, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent4×

Procedure

4 M HCl in dioxane (0.890 mL, 3.5 mmol) was added dropwise to a solution of tert-butyl methyl(2-methyl-2-morpholinopropyl)carbamate (970 mg, max. 2.98 mmol) in dry dioxane (5 mL) under a N2 atmosphere. The mixture was stirred at room temperature for 6 h. The mixture was evaporated to dryness and the residue was stirred in Et2O overnight. The solids were filtered off, rinsed with Et2O and dried on air to yield a white solid. The solids were dissolved in dry dioxane (2 mL) and 4 M HCl in dioxane (0.890 mL, 3.5 mmol) was added. The reaction mixture was stirred at room temperature overnight. The mixture was diluted with Et2O and the solids were filtered off, which resulted in AMN-39 (453 mg, 73% over 2 steps).

Workup

  1. customThe mixture was evaporated to dryness
  2. stirringthe residue was stirred in Et2O overnight
  3. filtrationThe solids were filtered off
  4. washrinsed with Et2O
  5. customdried on air
  6. customto yield a white solid
  7. stirringThe reaction mixture was stirred at room temperature overnight
  8. filtrationthe solids were filtered off
  9. customwhich resulted in AMN-39 (453 mg, 73% over 2 steps)

Sources & evidence

ORD record
ord-3b14258bb0d14f5ab3332e5ea5636b5b
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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