HCID 66911481, compound → Liafensine

HRID 1967430Notes

Reaction equation

HRID 1967430 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH2:13][C@@H:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([C:24]3[N:29]=[N:28][C:27]([NH2:30])=[CH:26][CH:25]=3)=[CH:9][CH:10]=2)[CH2:5]1>CO.O>[CH3:3][N:4]1[CH2:13][C@@H:12]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([C:24]3[N:29]=[N:28][C:27]([NH2:30])=[CH:26][CH:25]=3)=[CH:9][CH:10]=2)[CH2:5]1

Participants

3

Reactant 1

HCID 66911481HCID 66911481, compound

Product 1

HCID 58212050LiafensineYield 98.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of Compound 13 (550 g, 1.0 equiv) in 1:1 MeOH/DI water (16.5 L) was passed through a 1.2 micron in-line filter. The solution was stirred at ambient temperature as a 10% aq. NaHCO3 solution was slowly added. The batch became cloudy after 350 mL of the NaHCO3 solution had been added. Seed crystals (10.5 g) were then added, and the mixture was stirred for an additional 1 hour. More of the NaHCO3 solution (4 L) was added over 40 minutes. After the addition was complete, the mixture was stirred for 2 hours and then filtered. After conditioning on the filter under N2 for 1 hour, the wet filter cake was re-suspended in 8:2 DI water/MeOH (5.5 L), stirred for 2 hours, and then filtered. The filter cake was conditioned under N2 for 48 hours and then dried in vacuo at 35° C. for 48 hours to give 450 g of the Compound 2 as a white solid in 96% yield and >99% purity.

Workup

  1. filtrationin-line filter
  2. additionwas slowly added
  3. additionhad been added
  4. additionSeed crystals (10.5 g) were then added
  5. stirringthe mixture was stirred for an additional 1 hour
  6. additionMore of the NaHCO3 solution (4 L) was added over 40 minutes
  7. additionAfter the addition
  8. stirringthe mixture was stirred for 2 hours
  9. filtrationfiltered
  10. filtrationAfter conditioning on the filter under N2 for 1 hour
  11. stirringstirred for 2 hours
  12. filtrationfiltered
  13. customdried in vacuo at 35° C. for 48 hours

Sources & evidence

ORD record
ord-e2f619557802406cb7099386615aac8b
Source dataset
uspto-grants-2013_04
Patent number
US08420811B2

Reaction notes

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