Potassium Hydroxide → HCID 18675909, compound

HRID 1492870Notes

Reaction equation

HRID 1492870 reaction equation
[OH:1][CH:2]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:38])([CH3:37])[C:33]([O:35]C)=[O:34])=[CH:28][CH:27]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH:7]1[CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[K+]>C(O)C>[OH:1][CH:2]([C:26]1[CH:27]=[CH:28][C:29]([C:32]([CH3:38])([CH3:37])[C:33]([OH:35])=[O:34])=[CH:30][CH:31]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH:7]1[CH:13]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18675910HCID 18675910, compound

Product 1

HCID 18675909HCID 18675909, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-[1-hydroxy-4-(4-hydroxydiphenylmethyl-1-piperidinyl)butyl]-α,α-dimethylbenzeneacetate (1.2 gm) was combined with potassium hydroxide (0.4 gm) and ethanol (5 ml), and the mixture was heated to reflux for 7 hours. The ethanol was removed on a rotary evaporator and the residue was dissolved in water (2 ml). The aqueous solution was acidifed with glacial acetic acid to provide a solid which was recrystallized from 1:1 methanol/ethyl acetate to give 4-[1-hydroxy-4-(4-hydroxydiphenylmethyl-1-piperidinyl)butyl]-α,α-dimethylbenzeneacetic acid (terfenadine carboxylate).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 7 hours
  3. customThe ethanol was removed on a rotary evaporator
  4. dissolutionthe residue was dissolved in water (2 ml)
  5. customto provide a solid which
  6. customwas recrystallized from 1:1 methanol/ethyl acetate

Sources & evidence

ORD record
ord-f9e70331f60247e2b978070ab82bc425
Source dataset
uspto-grants-1994_12
Patent number
US05375693

Reaction notes

Loading…