Ammonia → N1-Isopropyl-N1-(4-methoxyphenyl)glycinamide

HRID 1599093Notes

Reaction equation

HRID 1599093 reaction equation
Br[CH2:2][C:3]([N:5]([CH:14]([CH3:16])[CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[O:4].[NH3:17]>CO>[NH2:17][CH2:2][C:3]([N:5]([CH:14]([CH3:16])[CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 107795342-Bromo-N-isopropyl-N-(4-methoxyphenyl)acetamide

Product 1

HCID 54496521N1-Isopropyl-N1-(4-methoxyphenyl)glycinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.86 g of 2-bromo-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (10 mmol) in 100 mL methanol was saturated with ammonia at 0° and left for 3 days at ambient temperature in a sealed flask. Methanol and ammonia were removed in vacuo and the residue was dissolved in 100 mL of chloroform and washed with water (2×50 mL). The organic layer was dried over anhydrous MgSO4, filtered, concentrated in vacuo and dried under high vacuum to afford 2.7 g of the title compound as an oil. 1H NMR (300 MHz, CDCl3) d 6.96 (m, 4H), 4.99 (m, 1H), 3.84 (s, 3H), 2.97 (s, 2H), 1.58 (s, 2H), 1.05 (d, 6H, J=6.6); low resolution MS (ESI)m/e 223 (MH+).

Workup

  1. customMethanol and ammonia were removed in vacuo
  2. dissolutionthe residue was dissolved in 100 mL of chloroform
  3. washwashed with water (2×50 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-99811414232746baaddd17af590f5a57
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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