Hydrochloric Acid → HCID 68712100, compound

HRID 2279938Notes

Reaction equation

HRID 2279938 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1)[C:3]#N.Cl.CC[O:22][CH2:23]C.C[OH:26]>>[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1)[C:3]([O:22][CH3:23])=[O:26]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3283Diethyl EtherHCID 12140598HCID 12140598, compound

Product 1

HCID 68712100HCID 68712100, compoundYield 70%

Procedure

To a stirred solution of 2-amino-2-(3-(benzyloxy)phenyl)acetonitrile (1.22 g, 5.3 mmol) in methanol (10 mL) at room temperature was added 2 N HCl in ether (10 mL, 20 mmol). The resulting mixture was heated under reflux for 18 h and concentrated to dryness. The crude material was taken up in ethyl acetate (200 mL) and washed with saturated aqueous sodium bicarbonate (100 mL). The layers were separated and the organic phase dried over magnesium sulfate, filtered and the solvent was removed in vacuo. The residue was loaded onto a SCX cartridge eluting with dichloromethane/methanol followed by 7N ammonia in methanol to afford the title compound (1.0 g, 70%) as a thick orange oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 18 h
  3. concentrationconcentrated to dryness
  4. washwashed with saturated aqueous sodium bicarbonate (100 mL)
  5. customThe layers were separated
  6. dry with materialthe organic phase dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. washeluting with dichloromethane/methanol

Sources & evidence

ORD record
ord-7976b44e76264ab1a8657544f9a8e61b
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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