Dimethylformamide → HCID 54511705, compound

HRID 1756778Notes

Reaction equation

HRID 1756778 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[C:4]([C@H:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][C:12](O)=[O:13])[CH:5]=[CH:6][CH:7]=2)[O:2]1.S(Cl)([Cl:22])=O.CN(C)C=O>C(Cl)Cl>[CH2:1]1[O:9][C:8]2[C:3](=[C:4]([C@H:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][C:12]([Cl:22])=[O:13])[CH:5]=[CH:6][CH:7]=2)[O:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 54473865HCID 54473865, compound

Product 1

HCID 54511705HCID 54511705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.3 g (4.9 mmol) of (R)-3-(2, 3-methylenedioxyphenyl) octanoic acid in 20 ml of methylene chloride were added 1.1 ml of thionyl chloride and 0.1 ml of N, N-dimethylformamide, and the resultant mixture was refluxed under stirring for 2 hours. The reaction mixture was concentrated in vacuo to give (R)-3-(2, 3-methylenedioxyphenyl) octanoyl chloride as an oil. This oil was dissolved in methylene chloride to give a solution, which was dropwise added to a solution of 1.08 g (4.9 mmol) of 2, 6-diisopropyl-3-dimethylaniline and 1.0 ml of triethylamine in 20 ml of methylene chloride (5°-10° C.). The reaction mixture was allowed to react at room temperature overnight and chromatographed on a silica gel column, eluting with ethyl acetate/hexane to give 1.16 g of gelatinous material. This was dissolved in acetone and mixed with 22% solution of hydrogen chloride in 2 ml of ethyl acetate. The resultant mixture (hydrochloride) was concentrated and crystallized from hexane to give 1.23 g of (R)-N-(2, 6-diisopropyl-3-dimethylaminophenyl)-3-(2, 3-methylenedioxyphenyl) octanamide hydrochloride. Yield, 50%.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-2683a0ec9460474b85379e7b95e540c0
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

Loading…