Formaldehyde → HCID 86759237, compound

HRID 479627Notes

Reaction equation

HRID 479627 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]2[C:18]([O:20][CH3:21])=[O:19])(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C=O.[C:24]([BH3-])#N.[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:24])[CH2:14][C@H:13]2[C:18]([O:20][CH3:21])=[O:19])(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86759238HCID 86759238, compound

Product 1

HCID 86759237HCID 86759237, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3,5-Dichlorobenzenesulfonyl)piperazine-2(S)-carboxylic acid, methyl ester (55 mg, 0.16 mmol) was added to a 5 mL round bottom flask containing 2 mL of acetonitrile and 37% formaldehyde (63 mg, 0.78 mmol) at 0°. Sodium cyanoborohydride (30 mg, 3 equivalents) was added portionwise over 10 minutes. The mixture was stirred at 25° for 2 hours. The solvent was removed under reduced pressure and the residue partitioned between methylene chloride and 1N HCl. The aqueous layer was neutralized with saturated sodium bicarbonate and extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent removed under reduced pressure. Flash chromatography on silica gel eluted with (98/2/0.1 methylene chloride/methanol/acetic acid) gave 38 mg of 1-(3,5-dichlorobenzenesulfonyl)-4-methyl-piperazine-2(S)-carboxylic acid, methyl ester. The methyl ester was hydrolysed and isolated as described in Example 39, Step F.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between methylene chloride and 1N HCl
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. washFlash chromatography on silica gel eluted with (98/2/0.1 methylene chloride/methanol/acetic acid)

Sources & evidence

ORD record
ord-50eb9fbc3050453f82e5cf982922e1a7
Source dataset
uspto-grants-2003_11
Patent number
US06645939B1

Reaction notes

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