Butyl iodide → HCID 20188685, compound

HRID 1789121Notes

Reaction equation

HRID 1789121 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][N:6]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH2:9][CH3:10].[CH2:18]([I:22])[CH2:19][CH2:20][CH3:21]>C(#N)C>[I-:22].[CH2:7]([N+:6]([CH2:5][C:4]1[CH:15]=[CH:16][CH:17]=[C:2]([OH:1])[CH:3]=1)([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 10962Butyl iodideHCID 201886883-[(Dibutylamino)methyl]phenol

Product 1

HCID 20188685HCID 20188685, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture was prepared containing 10 g (0.042 m) of 3-hydroxy N,N-dibutylbenzylamine, 15 g (0.082 m) of butyliodide and 25 ml of acetonitrile. The mixture was heated to reflux overnight. The completion of the reaction was determined by high pressure liquid chromatography. After completion, the solvent was removed and the residue triturated with ether, filtered and dried. The desired N,N,N-tributyl-(3-hydroxybenzyl)ammonium iodide product was recovered as a white powder in a yield of 15.7 g. The product melted at 128° C.-130° C. and its elemental analysis is as follows:

Workup

  1. customA mixture was prepared
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight
  4. customAfter completion, the solvent was removed
  5. customthe residue triturated with ether
  6. filtrationfiltered
  7. customdried
  8. customThe desired N,N,N-tributyl-(3-hydroxybenzyl)ammonium iodide product was recovered as a white powder in a yield of 15.7 g

Sources & evidence

ORD record
ord-8a6119e32beb49ab984ec47353dcc123
Source dataset
uspto-grants-1987_08
Patent number
US04687509

Reaction notes

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