Water → HCID 85835763, compound

HRID 2087097Notes

Reaction equation

HRID 2087097 reaction equation
O.[CH3:2][N:3]([C:5]([CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:7])[CH3:6])[CH3:4].[CH3:13][I:14]>ClCCl>[I-:14].[CH3:4][N+:3]([C:5]([CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:6])[CH3:7])([CH3:13])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 221336n,n,2,4,4-pentamethylpentan-2-amine

Product 1

HCID 85835763HCID 85835763, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled (water bath) solution of N,N-dimethyl t-octylamine (5 g, 31.8 mmol) in dichloromethane (30 mL) was added methyl iodide (6.7 g, 47.7 mmol) drop-wise. A slight increase in temperature was observed along with the formation light yellow precipitate. Stirring was continued for 24 h at room temperature, and at the end of this period, the solvent and excess methyl iodide were evaporated to produce a light yellow powder. This solid was washed with excess of n-pentane (3×75 mL), filtered, and suction dried (9.0 g, 95%). mp: ca. 260° C. (by DSC). 1H NMR (CDCl3): δ3.33 (s, 9H, —N+(CH3)3), 1.82 (s, 2H, —CH2—), 1.61 (bt, 6H, —C(CH3)2—), 1.12 (s, 9H, —C(CH3)3) ppm.

Workup

  1. temperatureA slight increase in temperature
  2. stirringStirring
  3. customat the end of this period, the solvent and excess methyl iodide were evaporated
  4. customto produce a light yellow powder
  5. washThis solid was washed with excess of n-pentane (3×75 mL)
  6. filtrationfiltered
  7. customsuction dried (9.0 g, 95%)

Sources & evidence

ORD record
ord-3454d70540bd43a696bff152248a355a
Source dataset
uspto-grants-2004_04
Patent number
US06727387B2

Reaction notes

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