Methyl iodide → Ethanaminium, 2-(4-((1Z)-1,2-diphenyl-1-buten-1-yl)phenoxy)-N,N,N-trimethyl-, iodide (1:1)

HRID 2287487Notes

Reaction equation

HRID 2287487 reaction equation
[CH3:1][CH2:2]/[C:3](/[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[C:4](/[C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[CH:15][CH:16]=1)\[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[CH3:29][I:30]>C(OCC)(=O)C>[CH3:1][CH2:2]/[C:3](/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[C:4](/[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N+:20]([CH3:29])([CH3:22])[CH3:21])=[CH:13][CH:12]=1)\[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[I-:30]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 2733526Tamoxifen

Product 1

HCID 3033898Ethanaminium, 2-(4-((1Z)-1,2-diphenyl-1-buten-1-yl)phenoxy)-N,N,N-trimethyl-, iodide (1:1)Yield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tamoxifen methiodide was prepared by reacting 2.0 g of tamoxifen (Aldrich Chemical Co., St. Louis, Mo.) with methyl iodide at 0° C. for 24 hours. Ethyl acetate was then added to afford a white precipitate, which was recrystallized from methanol to yield >99% tamoxifen methiodide. Tamoxifen benzyl bromide was synthesized by reacting tamoxifen with benzyl bromide.

Workup

  1. customTamoxifen methiodide was prepared
  2. customat 0° C.
  3. customfor 24 hours
  4. customto afford a white precipitate, which
  5. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-e970d2e129a54fbb8dc30652f47d3690
Source dataset
uspto-grants-2000_07
Patent number
US06083990

Reaction notes

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