Phosphoric Acid → Desvenlafaxine

HRID 1838488Notes

Reaction equation

HRID 1838488 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-3e12e273b4fc46a1ab009c77810cd8e7
Source dataset
uspto-grants-2004_01
Patent number
US06673838B2

Reaction notes

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