Methyl iodide → Iodide Ion

HRID 1044676Notes

Reaction equation

HRID 1044676 reaction equation
[CH3:1][N+:2]1([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:22])[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=43)[CH2:4][CH2:3]1)=[O:15].C1C2C[C@H]3N(CC4CC4)CC[C@]45[C@H](C(CC[C@@]34O)=O)OC(C=25)=C(O)C=1.C[I:53]>CC(C)=O>[I-:53].[CH3:1][N+:2]1([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([OH:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@:18]2([OH:21])[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 5360515NaltrexoneHCID 5361918Methylnaltrexone

Product 2

HCID 30165Iodide IonHCID 5361918Methylnaltrexone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

U.S. Pat. No. 4,176,186 discloses that methylnaltrexone is prepared by reacting naltrexone as raw material with methyl iodide in acetone as solvent in a closed vessel at 70° C. for 4 days to produce an iodide of MNTX after quaternization, and then performing an ion exchange. The two-step reaction has a yield of about 54%. The disadvantages of this method lie in that the raw material would not react completely; the raw material would form a salt and precipitate out during the process of the reaction; a qualified product would not be not ease to be obtained even after refining; moreover; and phenol alkylation byproducts would be generated.

Workup

  1. customis prepared
  2. customat 70° C.
  3. customfor 4 days

Sources & evidence

ORD record
ord-ce2050dadeda4171bcb93c03803e4a11
Source dataset
uspto-grants-2013_10
Patent number
US08563721B2

Reaction notes

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