Acetyl chloride → HCID 10082161, compound

HRID 898882Notes

Reaction equation

HRID 898882 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH2:13])[CH2:7][CH2:6]2.CCN(C(C)C)C(C)C.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:13][C:23](=[O:25])[CH3:24])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 199076-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamineHCID 81531Diisopropylethylamine

Product 1

HCID 10082161HCID 10082161, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 6-methoxy-1,2,3,4-tetrahydronaphthalen-2-ylamine (2.54 g; 14.3 mmol) in CH2Cl2 (20 mL) is added DIEA (3.4 mL) and the reaction mixture was cooled to 0° C. Acetyl chloride (1.22 mL; 17.1 mmol) is added dropwise at 0° C. and the reaction is allowed to warm to RT and stirred for 18 h. The reaction mixture was diluted with CH2Cl2, washed with H2O, dried over Na2SO4, filtered and the solvent removed under reduced pressure to provide a crude solid. Purification by flash chromatography (SiO2) eluting with hexanes-EtOAc affords 1.57 g (50%) of N-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide as a white solid.

Workup

  1. temperatureto warm to RT
  2. washwashed with H2O
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto provide a crude solid
  7. customPurification by flash chromatography (SiO2)
  8. washeluting with hexanes-EtOAc

Sources & evidence

ORD record
ord-6f011c6f9125493eb781835916f99ca5
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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