Phenylacetyl chloride → HCID 14348999, compound

HRID 2107695Notes

Reaction equation

HRID 2107695 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]([F:28])([F:27])[C:9]1[CH:26]=[CH:25][C:12]([O:13][CH:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1.C(N(CC)CC)C.[C:36]1([CH2:42][C:43](Cl)=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)(Cl)Cl>[C:36]1([CH2:42][C:43]([N:16]2[CH2:15][CH:14]([O:13][C:12]3[CH:25]=[CH:26][C:9]([C:8]([F:7])([F:27])[F:28])=[CH:10][CH:11]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17]2)=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 14348987HCID 14348987, compound

Product 1

HCID 14348999HCID 14348999, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a cooled solution of 2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine of Example 1 (5.8 g. 0.019 mole) and triethylamine (2.3 g, 0.023 mole) in chloroform (75 ml) was slowly dropped phenylacetyl chloride (3.5 g. 0.023 mole) in chloroform (10 ml). After stirring at ambient temperature overnight the reaction mixture was concentrated to an oil. The oil was dissolved in ether, then washed with water, dilute HCl (10%), again with water and dried (saturated NaCl, anhydrous MgSO4). The solution was filtered, concentrated to an oil which was extracted with boiling hexanes and then concentrated to an oil (6.8 g, 84%). A sample was distilled to yield an oil of 3-phenylacetyl-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine, 240°-250° C./0.1 mm.

Workup

  1. concentrationwas concentrated to an oil
  2. dissolutionThe oil was dissolved in ether
  3. washwashed with water, dilute HCl (10%), again with water
  4. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  5. filtrationThe solution was filtered
  6. concentrationconcentrated to an oil which
  7. extractionwas extracted with boiling hexanes
  8. concentrationconcentrated to an oil (6.8 g, 84%)
  9. distillationA sample was distilled

Sources & evidence

ORD record
ord-6df0399405a04f7c857578b787709de8
Source dataset
uspto-grants-1990_06
Patent number
US04935418

Reaction notes

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