Acetyl chloride → HCID 19888369, compound

HRID 654079Notes

Reaction equation

HRID 654079 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][C:10]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:11]=1[O:12][CH:13]1[CH2:16][NH:15][CH2:14]1.[C:22](Cl)(=[O:24])[CH3:23]>O1CCCC1>[C:22]([N:15]1[CH2:14][CH:13]([O:12][C:11]2[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:10]=2[CH3:9])[CH2:16]1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19888405HCID 19888405, compound

Product 1

HCID 19888369HCID 19888369, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (10.8 g, 106 mmol) was added to a stirred slurry of 3-(2,6-dimethylphenoxy)azetidine monohydrochloride (9.10 g, 42.7 mmol) in tetrahydrofuran (500 mL). After 10 minutes the reaction mixture was cooled to 0° C., and a solution of acetyl chloride (5.03 g, 64.1 mmol) in 50 mL of tetrahydrofuran was added dropwise. The reaction mixture was allowed to come to ambient temperature and was stirred overnight. The reaction mixture was then filtered and the filtrate concentrated in vacuo. The residue was chromatographed (flash, SiO2) eluting with methylene chloride/methanol (9:1) to give 9.00 g (99%) of yellow powder with a melting point of 40.0°-42.5° C.

Workup

  1. customto come to ambient temperature
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was chromatographed (flash, SiO2)
  5. washeluting with methylene chloride/methanol (9:1)

Sources & evidence

ORD record
ord-162994ce4cff44d0836ca061d3ba4f43
Source dataset
uspto-grants-1992_07
Patent number
US05130309

Reaction notes

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