2-Methoxybenzaldehyde → HCID 22674678, compound

HRID 1006364Notes

Reaction equation

HRID 1006364 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O.Cl.Cl.[CH:27]([CH:40]1[CH2:45][NH:44][CH2:43][CH2:42][N:41]1[CH3:46])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[CH:27]([CH:40]1[CH2:45][N:44]([CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[O:16][CH3:15])[CH2:43][CH2:42][N:41]1[CH3:46])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22674559HCID 22674559, compound

Product 1

HCID 22674678HCID 22674678, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 1M solution of sodium triacetoxyborohydride in N,N-dimethylformamide (75 μl) was added portionwise to a mixture of 2-methoxybenzaldehyde (7.5 mg) and a solution of 2-benzhydryl-1-methylpiperazine dihydrochloride (17.0 mg) in N,N-dimethylformamide (50 μl) at 0° C. and the whole was stirred at 0° C. to 5° C. for 1 hour and further at 5° C. to room temperature for 1 hour. The mixture was extracted with aqueous 0.25N sulfuric acid solution and washed with ethyl acetate. The combined solution was applied on solid phase extraction column cartridge (C18, 200 mg) and eluted with water and acetonitrile successively. The eluate was concentrated in vacuo to give 2-benzhydryl-4-(2-methoxybenzyl)-1-methylpiperazine (14.3 mg).

Workup

  1. extractionThe mixture was extracted with aqueous 0.25N sulfuric acid solution
  2. washwashed with ethyl acetate
  3. extractionThe combined solution was applied on solid phase extraction column cartridge (C18, 200 mg)
  4. washeluted with water and acetonitrile successively
  5. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-f52f9e9ab5104c17ba5580ae8fdbcfd1
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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