Hydrochloric Acid → HCID 68578451, compound

HRID 639514Notes

Reaction equation

HRID 639514 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[NH:19][CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13]4)[CH3:2].Cl.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[CH:28]=[CH2:29]>CN(C=O)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([CH2:29][CH:28]=[CH2:27])[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13]4)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 68576879HCID 68576879, compound

Product 1

HCID 68578451HCID 68578451, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-Ethylmorphinan.HCl 46 (3 mg, 0.01 mmol) in dry DMF (0.6 mL) was added potassium carbonate (5 mg, 0.036 mmol), allyl bromide (5.0 μL, 0.060 mmol) sequentially and the mixture was refluxed. After 2 h, the mixture was dried over anhydrous MgSO4, filtered, and concentrated. Column chromatography of the product gave -2 mg of white solid. 1H NMR (300 MHz, CDCl3) δ 6.89˜7.16 (3H, m); 5.80 (1H, d); 5.16˜5.30 (2H, m); 4.00˜4.30 (1H, dd); 3.68 (2H, t); 3.66 (1H, m); 3.15 (1H, br); 2.68 (2H, m); 2.50 (2H, m); 2.38 (1H, m); 1.10˜1.70 (13H, m).

Workup

  1. temperaturethe mixture was refluxed
  2. dry with materialthe mixture was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-10f71af7c82440e38b115ba3cbcfde6d
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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