Water → Oxybutynin

HRID 1895560Notes

Reaction equation

HRID 1895560 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][C:7]#[C:8][CH2:9][O:10][C:11]([C:13]([OH:26])([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:12])[CH2:4][CH3:5].Cl.O.CCCCCCC.[OH-].[Na+]>CCCCC>[CH3:1][CH2:2][N:3]([CH2:6][C:7]#[C:8][CH2:9][O:10][C:11]([C:13]([OH:26])([CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:12])[CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 14798Sodium HydroxideHCID 91505Oxybutynin hydrochloride

Product 1

HCID 4634Oxybutynin

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
42.5 °C

Procedure

Oxybutynin chloride (100 gm) was treated with DM water (500 ml) at 25-30° C. and heated to 40-45° C. to observe clear solution. n-Heptane (500 ml) was added to the solution and adjusted the pH of the mass to 10.0-11.0 using 5% sodium hydroxide solution at 20-25° C. Layers obtained were separated and aqueous layer was extracted with heptane. Organic layers were combined and concentrated under vacuum at 40-45° C. to give residue. n-Pentane (250 ml) was added to the residue and stirred under nitrogen atmosphere at 25-30° C. The solid product was filtered and washed with chilled n-pentane. Wet cake was dried at 40-42° C.

Workup

  1. customat 20-25° C
  2. customLayers obtained
  3. customwere separated
  4. extractionaqueous layer was extracted with heptane
  5. concentrationconcentrated under vacuum at 40-45° C.
  6. customto give residue
  7. filtrationThe solid product was filtered
  8. washwashed with chilled n-pentane
  9. customWet cake was dried at 40-42° C.

Sources & evidence

ORD record
ord-8f6a2ddc232b4e0b849e1326ebd757c3
Source dataset
uspto-grants-2013_08
Patent number
US08513455B2

Reaction notes

Loading…