Phosphoric Acid → Desvenlafaxine

HRID 860914

Reaction equation

HRID 860914 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 THIOPHENOXIDE

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-45fafbe0bbc64b9b947cd0b54ba8fe40
Source dataset
uspto-grants-2006_12
Patent number
US07154001B2

Linked notes

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