Chloroform → HCID 22791903, compound

HRID 1293512Notes

Reaction equation

HRID 1293512 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]3[CH2:14][C@H:15]4[N:27]([CH3:28])[CH2:26][CH2:25][C@:21]56[C:22]=3[C:23]=2[O:24][C@H:20]5[C@@H:19]([OH:29])[CH:18]=[CH:17][C@@H:16]46)C(=O)C2=CC=CC=C12.CN.C(Cl)(Cl)Cl>O>[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][C@H:15]3[N:27]([CH3:28])[CH2:26][CH2:25][C@:21]45[C:22]=2[C:23]=1[O:24][C@H:20]4[C@@H:19]([OH:29])[CH:18]=[CH:17][C@@H:16]35

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6329MethylamineHCID 69314272HCID 69314272, compound

Product 1

HCID 22791903HCID 22791903, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 14 g (29.6 mmol) of 3-O-phthalimidopropyl morphine (13) was added 188 mL of 2M ethanolic methylamine, and the reaction mixture was allowed to stir for 3.5 h at room temperature under nitrogen. The reaction mixture was poured into 650 mL of chloroform and 425 mL of cold water. The organic layer was separated, and the aqueous layer was extracted with 3×90 mL of chloroform. The chloroform layers were combined and extracted with 2×140 mL of 1N HCl. The aqueous extract was basified with 140 mL of 2.5 N NaOH and extracted with 3×300 mL of chloroform. The organic layer was dried (Na2SO4) and concentrated. The residue was crystallized from diethyl ether to give 8.9 g (26 mmol, 88%) of 14 as a white solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with 3×90 mL of chloroform
  3. extractionextracted with 2×140 mL of 1N HCl
  4. extractionThe aqueous extract
  5. extractionextracted with 3×300 mL of chloroform
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-3074be35d3ed42929f537c6eee55d875
Source dataset
uspto-grants-2007_07
Patent number
US07238791B1

Reaction notes

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