Dimethylamine → HCID 23362245, compound

HRID 1082125Notes

Reaction equation

HRID 1082125 reaction equation
[CH2:1]([N:3](CC)[CH2:4]C)C.[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]([CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30](O)=[O:31])=[CH:24][CH:23]=1)[CH3:18].ClC(OC)=O.CNC>O1CCCC1>[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]([CH2:19][CH2:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][C:30]([N:3]([CH3:4])[CH3:1])=[O:31])=[CH:26][CH:27]=1)[CH3:18]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 21700393HCID 21700393, compound

Product 1

HCID 23362245HCID 23362245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.4 mL) was added to an ice-cooled solution of 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]propanoic acid (1.00 g) in dry tetrahydrofuran (20 mL). The mixture was stirred at 0° C. during the addition of freshly distilled methyl chloroformate (0.25 mL), and stirring continued at this temperature for 45 minutes prior to the addition of a solution of dimethylamine in industrial methylated spirit (30% w/v; 20 mL). The mixture was stirred at room temperature for 20 hrs then evaporated. The residue was suspended in water (100 mL). Ethyl acetate (200 mL) and brine (100 mL) were added, the layers were separated and the aqueous layer extracted with ethyl acetate (2×200 mL). The combined ethyl acetate solutions were washed with brine (500 mL), dried (MgSO4) and evaporated. The resulting gum was chromatographed on silica gel with 1% methanol in dichloromethane as eluent to afford a gum which crystallised on standing to afford the title compound, mp 103°-5° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 20 hrs
  2. customthen evaporated
  3. additionEthyl acetate (200 mL) and brine (100 mL) were added
  4. customthe layers were separated
  5. extractionthe aqueous layer extracted with ethyl acetate (2×200 mL)
  6. washThe combined ethyl acetate solutions were washed with brine (500 mL)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe resulting gum was chromatographed on silica gel with 1% methanol in dichloromethane as eluent
  10. customto afford a gum which
  11. customcrystallised

Sources & evidence

ORD record
ord-2a9728e6466547488b59a8e6a5e6e767
Source dataset
uspto-grants-1996_12
Patent number
US05589492

Reaction notes

Loading…