Acetyl chloride → Triethylamine hydrochloride

HRID 1388342Notes

Reaction equation

HRID 1388342 reaction equation
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH3:11].[C:17]([Cl:20])(=[O:19])[CH3:18]>C(Cl)Cl>[C:17]([N:4]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][OH:9])[CH2:2][CH2:3]1)(=[O:19])[CH3:18].[ClH:20].[CH2:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH3:11]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 76771-(2-Hydroxyethyl)piperazineHCID 8471Triethylamine

Product 2

HCID 11130Triethylamine hydrochlorideHCID 47396291-Acetyl-4-(2-hydroxyethyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Piperazinoethanol (7.81 g, 60 mmoles) and triethylamine (8.36 ml, 66 mmoles) were dissolved in 100 ml of methylene chloride and cooled to 0°-5° C. Acetyl chloride (4.28 ml, 60 mmoles) in 20 ml of methylene chloride was added and the reaction mixture warmed to room temperature, held for 2 hours, and then evaporated in vacuo to dry solids. The solids were triturated with four portions of warm ether. The triturates were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to yield 2-(4-acetylpiperazino)ethanol as an oil [7.5 g; free of triethylamine and triethylamine hydrochloride by pnmr assay; Rf 0.3 (methanol/10% acetic acid)].

Workup

  1. temperaturecooled to 0°-5° C
  2. customevaporated in vacuo
  3. customto dry solids
  4. customThe solids were triturated with four portions of warm ether
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c2cff0420fb745d58ae32f2ecd67871b
Source dataset
uspto-grants-1984_02
Patent number
US04431649

Reaction notes

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