Chloroform → 2-(Naphthalen-1-yl)acetyl chloride

HRID 566232Notes

Reaction equation

HRID 566232 reaction equation
[C:1]1([CH2:11][C:12]([OH:14])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)[Cl:16]>>[C:1]1([CH2:11][C:12]([Cl:16])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 6212Chloroform2×HCID 68621-Naphthaleneacetic Acid

Product 1

HCID 27953862-(Naphthalen-1-yl)acetyl chloride

Procedure

1-Naphthylacetyl chloride is prepared according to the method described in Example 8 using 1-naphthylacetic acid (2.47 g, 13.3 mmol) to give a yellow oil which is dissolved in chloroform (10 mL). This solution is added to a solution of (±)-trans-[2-(4-methyl-1-piperazinyl)]cyclohexanol (2.5 g, 12.6 mmol) in chloroform (10 mL), and the mixture is refluxed for 11 hours under nitrogen. The crude free ester is isolated as described in Example 13, and is converted to the monohydrochloride salt in ether/dichloromethane (35 mL, 6:1) by treatment with 1 equivalent of HCl in the same solvent. The resulting solid is washed with ether and recrystallised from hot ethyl acetate/methanol to yield the title compound.

Workup

  1. customto give a yellow oil which
  2. temperaturethe mixture is refluxed for 11 hours under nitrogen
  3. customThe crude free ester is isolated

Sources & evidence

ORD record
ord-cc4cbd32dbf443f09c6d70b4920a9fb6
Source dataset
uspto-grants-2001_01
Patent number
US06174879B1

Reaction notes

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