Carbon Dioxide → 1-[2-(4-Hydroxyphenylamino)benzoyl]piperidine

HRID 464789Notes

Reaction equation

HRID 464789 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[CH:27]=[CH:26][CH:25]=[CH:24][C:15]=2[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])=[CH:9][CH:8]=1.C(=O)=O.C(O)(C)C>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14]2[CH:27]=[CH:26][CH:25]=[CH:24][C:15]=2[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 3776IsopropanolHCID 25134Boron tribromideHCID 135056301-[2-(4-Methoxyphenylamino)benzoyl]piperidine

Product 1

HCID 135056311-[2-(4-Hydroxyphenylamino)benzoyl]piperidineYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (10 ml in 25 ml of methylene dichloride) was added dropwise over a 30 minute period to a solution of 15.5 g of 1-[2-(4-methoxyphenylamino)benzoyl]piperidine in 80 ml of dry methylene dichloride cooled in a bath of Dry Ice and isopropyl alcohol. The reaction mixture was allowed to warm to room temperature and to stand overnight. The solvent was then removed in vacuo, and the residue was treated with 100 ml of distilled water and made basic with about 250 ml of saturated sodium bicarbonate solution. The solid which formed was collected by filtration and recrystallized from ethanol to give 10.2 g of 1-[2-(4-hydroxyphenylamino)benzoyl]piperidine, colorless powder, m.p. 199°-201° C. (decompn.).

Workup

  1. customThe solvent was then removed in vacuo
  2. additionthe residue was treated with 100 ml of distilled water
  3. customThe solid which formed
  4. filtrationwas collected by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7693cbdf245f4970af51fe0ce63014f4
Source dataset
uspto-grants-1985_10
Patent number
US04549016

Reaction notes

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