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

HRID 1418880Notes

Reaction equation

HRID 1418880 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-5b103113532245d9bca3c1db7be7107d
Source dataset
uspto-grants-1999_03
Patent number
US05885984

Reaction notes

Loading…