Formic Acid → HCID 86603914, compound

HRID 860916

Reaction equation

HRID 860916 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]([C:13]1([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)[CH3:3].[CH:20]([OH:22])=[O:21]>C(O)C>[CH3:1][N:2]([CH2:4][CH:5]([C:13]1([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)[CH3:3].[CH:20]([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 125017Desvenlafaxine

Product 1

HCID 86603914HCID 86603914, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of O-desmethylvenlafaxine (23.9 g), 96 wt % formic acid (4.79 g) and 2B ethanol (100 mL) was evaporated to give a syrupy residue. This material was redissolved in 2 B ethanol (100 mL) and evaporated to give a solid, which upon trituration in ether (200 mL) followed by filtration and vacuum drying (18 h; 50° C.; 50 mmHg) gave 27 g of product. This material was recrystallized from a hot solution of methanol (30 mL) and acetone (400 mL), which upon cooling to room temperature followed by filtering and vacuum drying (18 h; 50° C.; 50 mmHg) gave 20 g (71.2% yield) of product. m.p. 151° C.

Workup

  1. customwas evaporated
  2. customto give a syrupy residue
  3. customevaporated
  4. customto give a solid, which upon trituration in ether (200 mL)
  5. filtrationfollowed by filtration and vacuum
  6. customdrying (18 h; 50° C.; 50 mmHg)

Sources & evidence

ORD record
ord-937eab99684a4224a7ca7c7f2c8a88a6
Source dataset
uspto-grants-2006_12
Patent number
US07154001B2

Linked notes

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