Ammonium Chloride → HCID 86600279, compound

HRID 1441509Notes

Reaction equation

HRID 1441509 reaction equation
ClO.[CH2:3]([N:6]1[CH2:25][CH2:24][C@:13]23[C:14]4[C:15]5[O:23][C@H:12]2[C:11](=[O:26])[CH2:10][CH2:9][C@@:8]3([O:27][CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:7]1[CH2:20][C:19]=4[CH:18]=[CH:17][C:16]=5[O:21][CH3:22])C=C.[Cl-].[NH4+]>[Zn].CO>[OH:23][C:15]1[C:14]2[C@:13]34[CH2:24][CH2:25][N:6]([CH3:3])[C@@H:7]([C@:8]3([O:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:9][CH2:10][C:11](=[O:26])[CH2:12]4)[CH2:20][C:19]=2[CH:18]=[CH:17][C:16]=1[O:21][CH3:22]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 131727870HCID 131727870, compound

Product 1

HCID 86600279HCID 86600279, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4,5α-epoxy-3-methoxy-17-methyl-14-[(3-phenylpropyl)oxy]-morphinan-6-one (=14-O-(3-phenylpropyl)oxycodon) (see Example 1) (600 mg, 1.4 mmol), ammonium chloride (0.97 g, 18.0 mmol) and 30 ml MeOH was reflux heated under stirring. Then within 5 minutes activated zinc powder (0.94 g, 14.0 mmol) was added in portions and the mixture reflux heated for 6 h. After filtration from the inorganic residue, the filtrate was evaporated down, alkalised with conc. NH4OH, extracted with CH2Cl2 (3×40 ml), washed with H2O, dried over Na2SO4 and evaporated down. The evaporation residue (605 mg) was crystallised out of a little MeOH. Yield: 562 mg (86%) of compound 25. Fp. >258° C. (decomp.); IR (KBr): 3145 (OH), 1734 (CO) cm−1; 1H-NMR (CDCl3): δ 7.37-7.05 (m, 5 arom. H), 6.64 (d, 1 arom. H, J=8.3 Hz), 6.54 (d, 1 arom. H, J=8.3 Hz), 3.79 (s, OCH3), 2.30 (s, NCH3); MS (CI): m/z 436 (M++1).

Workup

  1. temperaturewas reflux
  2. temperatureheated
  3. temperaturethe mixture reflux
  4. temperatureheated for 6 h
  5. filtrationAfter filtration from the inorganic residue
  6. customthe filtrate was evaporated down
  7. extractionextracted with CH2Cl2 (3×40 ml)
  8. washwashed with H2O
  9. dry with materialdried over Na2SO4
  10. customevaporated down
  11. customThe evaporation residue (605 mg) was crystallised out of a little MeOH

Sources & evidence

ORD record
ord-69e2308234e6415cb5d8a5909331b62b
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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