Phosphoric Acid → Desvenlafaxine

HRID 891029Notes

Reaction equation

HRID 891029 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]([C:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:6]1[CH:7]=[CH:8][C:9]([O:12]C)=[CH:10][CH:11]=1)[CH3:3].[Na].C1(S)C=CC=CC=1.OP(O)(O)=O>O>[CH3:1][N:2]([CH2:4][CH:5]([C:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)[CH3:3]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 5656VenlafaxineHCID 66586497Sodium benzenethiol

Product 1

HCID 125017Desvenlafaxine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

Venlafaxine (5.6 g) and benzenethiol sodium salt (6.9 g) are charged to PEG 400 (25 g). The reaction mixture is heated to 160° C. for 5 hours. Then the temperature is lowered and water is added (60 g). The pH is adjusted to 3.5 with H3PO4. The organic by-products are removed by extraction with heptanes (25 g). The pH of the aqueous layer is then adjusted to 9.5 with aqueous ammonia. The precipitate is collected by suction filtration, re-slurried in water (100 g), isolated by suction filtration and dried in vacuo.

Workup

  1. customThe organic by-products are removed by extraction with heptanes (25 g)
  2. filtrationThe precipitate is collected by suction filtration, re-slurried in water (100 g)
  3. customisolated by suction filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-583b6e5fb82043499ad61da94a93ee34
Source dataset
uspto-grants-2006_02
Patent number
US07001920B2

Reaction notes

Loading…