Acetic Acid → HCID 10298483, compound

HRID 2115035Notes

Reaction equation

HRID 2115035 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:25])[C:10](=[O:24])[N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)[CH:5]=[CH:6][CH:7]=1.[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O)(=O)C.[Cl:38]C(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)([O-])O.[Na+]>[ClH:38].[CH2:26]([NH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:25])[C:10]([N:11]2[CH2:12][CH2:13][CH:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][CH2:16]2)=[O:24])[CH:5]=[CH:6][CH:7]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 69100250HCID 69100250, compound

Product 1

HCID 10298483HCID 10298483, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 0.51 g (1.5 mmol) of N-(3-aminophenyl)-2-(4-benzyl-piperidin-1-yl)-oxo-acetamide (Example 11), 0.15 ml (1.5 mmol) of benzaldehyde, 0.18 ml (3 mmol) of acetic acid in 15 ml of dichloroethane 0.48 g (2.25 mmol) of sodium triacetoxyborohydride (Aldrich) is added in small portions below 20° C., and the reaction mixture is stirred at room temperature for 2 hours. Then 30 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 30 ml of chloroform. The combined organic layers are dried over sodium sulfate, concentrated and the residue is purified by column chromatography using Kieselgel 60 as adsorbent (Merck) and ethyl acetate:hexane=1:2 as eluent. The product is treated with 2.5 N hydrochloric acid in ethyl acetate solution to yield 0.25 g (36%) of the title compound. Melting Point: 190-207° C. (dec.) (ethyl acetate)

Workup

  1. customthe organic layer is separated
  2. extractionthe water phase is extracted three times with 30 ml of chloroform
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue is purified by column chromatography
  6. additionThe product is treated with 2.5 N hydrochloric acid in ethyl acetate solution

Sources & evidence

ORD record
ord-b855a24899d543a19b99720ee318be52
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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