Dimethylamine → HCID 15491028, compound

HRID 362848Notes

Reaction equation

HRID 362848 reaction equation
[CH3:1][NH:2][CH3:3].[F:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11]/[C:12]/2=[CH:15]\[C:16](Cl)=[O:17])=[CH:7][CH:6]=1>ClCCl.C(OCC)(=O)C>[F:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11]/[C:12]/2=[CH:15]\[C:16]([N:2]([CH3:3])[CH3:1])=[O:17])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 86753732HCID 86753732, compound

Product 1

HCID 15491028HCID 15491028, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Dimethylamine (3 ml, 0.045 mol, Kodak) was added to a chilled (ice bath) solution of (E)-2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthylidene)acetyl chloride (2.3 g, 0.010 mol) in dichloromethane (35 ml). The reaction was warmed to 25° C. and stirred for 1.5 h. The volatiles were removed by spin evaporation in vacuo to give a beige residue. This residue was dissolved in ethyl acetate (200 ml), washed with deionized water (50 ml), and the organic layer was concentrated by spin evaporation in vacuo. The residue was chromatographed on Silica Gel 60 using a step gradient from ethyl acetate-hexanes/1:5 to ethyl acetate. Fractions containing (E)-2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthylidene)-N,N-dimethylacetamide were combined and concentrated by spin evaporation in vacuo to a white solid. Recrystallization from dichloromethane-hexanes gave 1.62 g (70%) of (E)-2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthylidene)-N,N-dimethylacetamide as a white crystalline solid; m.p., 66°-70° C.

Workup

  1. customThe volatiles were removed by spin evaporation in vacuo
  2. customto give a beige residue
  3. washwashed with deionized water (50 ml)
  4. concentrationthe organic layer was concentrated by spin evaporation in vacuo
  5. customThe residue was chromatographed on Silica Gel 60 using a step gradient from ethyl acetate-hexanes/1:5 to ethyl acetate
  6. additionFractions containing (E)-2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthylidene)-N,N-dimethylacetamide
  7. concentrationconcentrated by spin evaporation in vacuo to a white solid
  8. customRecrystallization from dichloromethane-hexanes

Sources & evidence

ORD record
ord-4a2382c8312c4a108169b580272381ee
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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