Acetyl chloride → 1-(Azocan-1-yl)ethan-1-one

HRID 259751Notes

Reaction equation

HRID 259751 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].C(Cl)(=[O:10])C.O1C[CH2:15][CH2:14][CH2:13]1>>[C:1]([N:3]1[CH2:6][CH2:7][CH2:15][CH2:14][CH2:13][CH2:5][CH2:4]1)(=[O:10])[CH3:2]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8028Tetrahydrofuran2×HCID 8471Triethylamine

Product 1

HCID 134292821-(Azocan-1-yl)ethan-1-one

Procedure

To a stirred solution of heptamethyleneimine (5.56 ml; 44 mmol) and triethylamine (6.13 ml; 44 mmol) in tetrahydrofuran (20 ml) under nitrogen at 0° C. was added dropwise a solution of acetyl chloride (3.13 ml; 44 retool) in tetrahydrofuran (20 ml). The reaction mixture was then warmed to room temperature and stirred for 1 hr. The resulting solid was filtered off and washed thoroughly with ether. The filtrate was evaporated in vacuo to give an orange oil. Distillation in vacuo gave the title compound (D9).

Workup

  1. filtrationThe resulting solid was filtered off
  2. washwashed thoroughly with ether
  3. customThe filtrate was evaporated in vacuo
  4. customto give an orange oil
  5. distillationDistillation in vacuo

Sources & evidence

ORD record
ord-81e31281b4be49f29f927bbb73481f98
Source dataset
uspto-grants-1996_06
Patent number
US05523299

Reaction notes

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