Acetic Acid → HCID 69100503, compound

HRID 2115103Notes

Reaction equation

HRID 2115103 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:26])[CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH:7]=[CH:8][CH:9]=1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(=O)C.ClC(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)([O-])O.[Na+]>[CH2:27]([NH:3][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:26])[CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH:7]=[CH:8][CH:9]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 69099963HCID 69099963, compound

Product 1

HCID 69100503HCID 69100503, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 0.32 g (1 mmol) of N-(3-amino-phenyl)-2-(4-benzyl-piperidin-1-yl)-acetamide (Example 175), 0.1 ml (1 mmol) of benzaldehyde, 0.12 ml (2 mmol) of acetic acid in 10 ml of dichloroethane 0.32 g (1.5 mmol) of sodium triacetoxyborohydride is added in small portions below 20° C., and the reaction mixture is stirred at room temperature for 2 hours. Then 20 ml of 8% sodium hydrogencarbonate solution is added to the mixture. The organic layer is separated and the water phase is extracted three times with 10 ml of dichloromethane. The combined organic layers are washed with 20 ml of water and dried over sodium sulfate, concentrated, the residue is treated with diethylether and the precipitated crystals are filtered off to yield 0.26 g (63%) of the title compound. Melting Point: 112-114° C. (ethyl acetate)

Workup

  1. customThe organic layer is separated
  2. extractionthe water phase is extracted three times with 10 ml of dichloromethane
  3. washThe combined organic layers are washed with 20 ml of water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. additionthe residue is treated with diethylether
  7. filtrationthe precipitated crystals are filtered off

Sources & evidence

ORD record
ord-af3875c6fc504eaba83aac25cea60f61
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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