4'-Chloropropiophenone → HCID 13882446, compound

HRID 1583318Notes

Reaction equation

HRID 1583318 reaction equation
[Mg].[N:2]1([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](O)=[C:14](Br)[CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:30])[CH2:28][CH3:29])=[CH:23][CH:22]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][CH2:8][N:2]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)=[CH:13][CH:14]=2)([OH:30])[CH2:28][CH3:29])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 226974'-ChloropropiophenoneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 20260687HCID 20260687, compound

Product 1

HCID 13882446HCID 13882446, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a Grignard reactant prepared from 1.82 g. of magnesium turnings and 22.3 g. of 4-[3-(piperidin-1-yl)-propoxy]-bromophenol in 100 ml. of dry tetrahydrofuran a solution of 8.4 g. of p-chloropropiophenone in 30 ml. of tetrahydrofuran is added dropwise, under slight reflux. The reaction mixture is slightly boiled for an additional hour, whereupon it is cooled and decomposed with a saturated aqueous ammonium chloride solution. The aqueous phase is extracted with tetrahydrofuran, the tetrahydrofuran phase is washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo. Crystallization of the residue from a mixture of n-hexane and ethyl acetate yields 12.2 g. of the named compound, melting at 104° to 105° C.

Workup

  1. waitThe reaction mixture is slightly boiled for an additional hour, whereupon it
  2. temperatureis cooled
  3. extractionThe aqueous phase is extracted with tetrahydrofuran
  4. washthe tetrahydrofuran phase is washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness in vacuo
  7. customCrystallization of the residue
  8. additionfrom a mixture of n-hexane and ethyl acetate
  9. customyields 12.2 g

Sources & evidence

ORD record
ord-0a3cc16e42b14ab6a9381e079e9c9dd8
Source dataset
uspto-grants-1985_11
Patent number
US04551465

Reaction notes

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