Formaldehyde → HCID 68752079, compound

HRID 1864803Notes

Reaction equation

HRID 1864803 reaction equation
C=O.[Br:3][C:4]1[CH:5]=[CH:6][C:7]([F:25])=[C:8]([C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@@H:13]2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[O:11])[CH:9]=1.[C:26](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([F:25])=[C:8]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH3:26])[CH2:14][C@@H:13]2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[O:11])[CH:9]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68750492HCID 68750492, compound

Product 1

HCID 68752079HCID 68752079, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Formaldehyde (1.47 mL, 19.4 mmol of 37% aqueous solution) was added to (5-Bromo-2-fluoro-phenyl)-[(S)-2-(4-fluoro-phenyl)-piperazin-1-yl]-methanone (0.32 g, 0.65 mmol) in 10 mL of methanol. The mixture was stirred at ambient temperature for 1 h and then sodium triacetoxyborohydride (0.82 g, 3.9 mmol) was added and the resulting mixture was stirred overnight. The volatiles were removed in vacuo, and the residue was portioned between ethyl acetate and 1M sodium bicarbonate solution. The organic phase was washed with 1M sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and concentrated to leave 0.21 g of product. LC/MS: Retention time, 2.14 min; (M+H)=395/397.

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. customThe volatiles were removed in vacuo
  3. washThe organic phase was washed with 1M sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eba87d2212064e9d925aeb5c6e6ac4cd
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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