Sodium Hydroxide → Morphine

HRID 1764042Notes

Reaction equation

HRID 1764042 reaction equation
[CH3:1][N:2]1[C@@H:18]2[CH2:19][C:7]3[CH:8]=[CH:9][C:10]([O:21]C)=[C:11]4[O:12][C@H:13]5[C@@H:14]([OH:20])[CH:15]=[CH:16][C@@H:17]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1.Cl.N1C=CC=CC=1.[OH-].[Na+]>O>[CH:8]1[C:7]2[CH2:19][C@H:18]3[N:2]([CH2:3][CH2:4][C@@:5]45[C@H:17]3[CH:16]=[CH:15][C@H:14]([OH:20])[C@@H:13]4[O:12][C:11]([C:6]=25)=[C:10]([OH:21])[CH:9]=1)[CH3:1]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5284371Codeine2×HCID 10176127Pyridinium chloride2×

Product 1

HCID 5288826Morphine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Rapoport et al. (J.A.C.S. 5485 and 5900 73 1951) have claimed a 22% yield of morphine from codeine employing pyridine hydrochloride as the cleavage agent. 1.00g codeine was heated with pyridine hydrochloride for six minutes under nitrogen. The reaction mixture was dissolved in 20ccm water, basified with 10ccm 4N NaOH and extracted with chloroform to yield 0.210g morphine.

Workup

  1. extractionextracted with chloroform

Sources & evidence

ORD record
ord-14495493d17d402dbe5de0701e4cca38
Source dataset
uspto-grants-1978_09
Patent number
US04114314

Reaction notes

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