Acetyl chloride → HCID 13039264, compound

HRID 851047Notes

Reaction equation

HRID 851047 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][C@H:8]2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>C(Cl)(Cl)Cl>[C:29]([O:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][C@H:8]2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:4][CH:3]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 70481907HCID 70481907, compound

Product 1

HCID 13039264HCID 13039264, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 3.21 g of trans-4-(4-hydroxyphenoxy)-1-methyl-3-phenylpiperidine in 150 ml of dry chloroform containing 1.72 ml of triethylamine is cooled in a cold water bath under nitrogen while 0.88 ml of acetyl chloride is added via syringe. After 3.5 hours at room temperature another 0.43 ml of triethylamine and 0.22 ml of acetyl chloride are added. After an additional 30 minutes stirring, the solvent is removed in vacuo and the residue is triturated with a mixture of ether (150 ml) and hexane (100 ml). The mixture is then filtered and the solid washed once with ether. The filtrate is concentrated in vacuo to an oil which crystallizes upon standing to a pale yellow oily solid. The oil is dissolved in 50 ml of boiling hexane and filtered. The filtrate is concentrated in vacuo to an oil which crystallizes under high vacuum to a nearly colorless, crystalline solid. The solid is dissolved in 25 ml of boiling hexane and the solution is allowed to cool. After standing overnight at room temperature the mixture is filtered, the solid washed with hexane and dried to afford product as colorless crystals, mp 79.5°-82° C.

Workup

  1. additionis added via syringe
  2. customthe solvent is removed in vacuo
  3. customthe residue is triturated with a mixture of ether (150 ml) and hexane (100 ml)
  4. filtrationThe mixture is then filtered
  5. washthe solid washed once with ether
  6. concentrationThe filtrate is concentrated in vacuo to an oil which
  7. customcrystallizes
  8. dissolutionThe oil is dissolved in 50 ml of boiling hexane
  9. filtrationfiltered
  10. concentrationThe filtrate is concentrated in vacuo to an oil which
  11. customcrystallizes under high vacuum to a nearly colorless, crystalline solid
  12. dissolutionThe solid is dissolved in 25 ml of boiling hexane
  13. temperatureto cool
  14. waitAfter standing overnight at room temperature
  15. filtrationthe mixture is filtered
  16. washthe solid washed with hexane
  17. customdried
  18. customto afford product as colorless crystals, mp 79.5°-82° C.

Sources & evidence

ORD record
ord-a98635b5cbc540cfa5e8a0603c79a6d5
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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