Triethylamine → HCID 19028921, compound

HRID 1781516Notes

Reaction equation

HRID 1781516 reaction equation
[CH:1]([NH:3][CH2:4][C:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][CH2:7][CH2:8]I)=[O:2].Cl.[CH3:23][NH:24][CH3:25].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:23][N:24]([CH2:8][CH2:7][CH2:6][C:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:4][NH:3][CH:1]=[O:2])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 19028885HCID 19028885, compound

Product 1

HCID 19028921HCID 19028921, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-formylamino-1-iodo-4,4-diphenylpentane (8.5 g), dimethylamine hydrochloride (17.63 g), triethylamine (30.1 ml), and potassium carbonate (3 g) was heated in acetonitrile (250 ml) at 60° C. for 2 hours. This reaction mixture was concentrated to dryness and the group was extracted using ethyl acetate and water. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated to dryness. The group was crystallized from ethyl acetate-isopropyl ether to provide the title compound (4.5 g) as white powder.

Workup

  1. concentrationThis reaction mixture was concentrated to dryness
  2. extractionthe group was extracted
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe group was crystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-512e99f9a9254acd8ab4b706e0bfbb8f
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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