Hydrochloric Acid → 1-Acetyl-3-[2-acetoxy-4-(1,1-dimethylheptyl)phenyl]piperidine

HRID 26079Notes

Reaction equation

HRID 26079 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[C:12]([OH:22])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].N1C=CC=CC=1.[C:29](OC(=O)C)(=[O:31])[CH3:30].Cl.[C:37](OCC)(=[O:39])[CH3:38]>>[C:29]([N:18]1[CH2:19][CH2:20][CH2:21][CH:16]([C:13]2[CH:14]=[CH:15][C:10]([C:2]([CH3:1])([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][C:12]=2[O:22][C:37](=[O:39])[CH3:38])[CH2:17]1)(=[O:31])[CH3:30]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 155715583-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]piperidine

Product 1

HCID 204997791-Acetyl-3-[2-acetoxy-4-(1,1-dimethylheptyl)phenyl]piperidine

Procedure

To a solution of 2.0 g. of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]piperidine in 20 ml. of pyridine at 10° C. is added 20 ml. of acetic anhydride and the mixture stirred under nitrogen for 18 hours. It is then poured onto ice/water and acidified with dilute hydrochloric acid. The product is isolated by extraction with ethyl acetate (2 × 100 ml.). The combined extracts are washed with brine, dried (MgSO4) and evaporated to give the product as an oil.

Workup

  1. additionIt is then poured onto ice/water
  2. washThe combined extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-38894303669d459dbe1bbe5890958843
Source dataset
uspto-grants-1979_04
Patent number
US04147872

Reaction notes

Loading…