Acetyl chloride → HCID 70417938, compound

HRID 2231835Notes

Reaction equation

HRID 2231835 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][NH:11][C:10](=[O:14])[C@H:9]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.[C:21](Cl)(=[O:23])[CH3:22].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:21]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][NH:11][C:10](=[O:14])[C@H:9]2[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:4][CH:3]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 13852697HCID 13852697, compound

Product 1

HCID 70417938HCID 70417938, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To 2.67 g (0.01 mol) of trans-4-(4-hydroxyphenyl)-3-phenyl-2-piperidone 27 dissolved in 20 cm3 of anhydrous pyridine, 2 cm3 (0.028 mol) of acetyl chloride are added under nitrogen at 0° C. The mixture is stirred for 2 hours 30 mins at 0° C., and then 48 hours at room temperature. The reaction mixture is then poured onto 50 g of ice. A spatulaful of sodium bicarbonate is added, and the mixture is stirred and then extracted with methylene chloride (3 times 60 cm3).

Workup

  1. custom48 hours
  2. customat room temperature
  3. stirringthe mixture is stirred
  4. extractionextracted with methylene chloride (3 times 60 cm3)

Sources & evidence

ORD record
ord-c3d7eaf7da8e49638c3a9fb585514b42
Source dataset
uspto-grants-1988_11
Patent number
US04785007

Reaction notes

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