1-Chloro-2-(diethylamine)ethane hydrochloride → HCID 10212316, compound

HRID 429339Notes

Reaction equation

HRID 429339 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:25]=[C:26]([I:29])[C:27]=1[OH:28])[C:5]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]=1[CH2:16][CH2:17][C:18]([O:20][CH:21]([CH2:23][CH3:24])[CH3:22])=[O:19])=[O:6].Cl.[CH2:31]([N:33]([CH2:36][CH2:37]Cl)[CH2:34][CH3:35])[CH3:32].[OH-].[Na+]>C(Cl)Cl.O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[I:29][C:26]1[CH:25]=[C:4]([CH:3]=[C:2]([I:1])[C:27]=1[O:28][CH2:32][CH2:31][N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[C:5]([C:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]=1[CH2:16][CH2:17][C:18]([O:20][CH:21]([CH2:23][CH3:24])[CH3:22])=[O:19])=[O:6]

Participants

7

Reactant 3

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14798Sodium HydroxideHCID 18355456HCID 18355456, compound

Product 1

HCID 10212316HCID 10212316, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

619 g of compound 7 and 180 g of diethylaminoethyl chloride, hydrochloride salt, are dissolved in 2L of methylene chloride and 500 ml of water. To this add 23 g of benzyltriethylammonium chloride and 80 g of sodium hydroxide in 2L of water. Stir vigorously for 5 hours. Keep the organic phase. Wash with 1 L of water. Dry over sodium sulfate. Filter. Evaporate.

Workup

  1. washWash with 1 L of water
  2. dry with materialDry over sodium sulfate
  3. filtrationFilter
  4. customEvaporate

Sources & evidence

ORD record
ord-0cc6024e745a4b90bb1bdda087cd3c9e
Source dataset
uspto-grants-2001_11
Patent number
US06316487B1

Reaction notes

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