Formaldehyde → HCID 68750684, compound

HRID 1864796Notes

Reaction equation

HRID 1864796 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Br:15][C:16]1[CH:17]=[C:18]([CH2:22][N:23]2[CH2:28][CH2:27][NH:26][CH2:25][C@@H:24]2[C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH:19]=[N:20][CH:21]=1.C=O>CO>[Br:15][C:16]1[CH:17]=[C:18]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH3:1])[CH2:25][C@@H:24]2[C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH:19]=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68748513HCID 68748513, compound

Product 1

HCID 68750684HCID 68750684, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium triacetoxyborohydride (1.5 g, 7 mmol) was added to a mixture of (S)-1-(5-bromo-pyridin-3-ylmethyl)-2-(4-fluoro-phenyl)-piperazine (as tris(trifluoroacetate) salt) (820 mg, 1.2 mmol) and formaldehyde (37% aqueous solution, 3 mL, 36.9 mmol) in 20 mL of methanol. The mixture was stirred at ambient temperature overnight, and then the volatiles were removed in vacuo and the residue dissolved in water and the pH was adjusted to 11 by the addition of 10 M sodium hydroxide solution. The product was extracted into dichloromethane and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to leave 431 mg of product. LC/MS: Retention time, 2.15 min; (M+H)=366.

Workup

  1. customthe volatiles were removed in vacuo
  2. dissolutionthe residue dissolved in water
  3. additionthe pH was adjusted to 11 by the addition of 10 M sodium hydroxide solution
  4. extractionThe product was extracted into dichloromethane
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ba6926768909430fa9231d040bf69e02
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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