Acetic Acid → HCID 69100529, compound

HRID 2115043Notes

Reaction equation

HRID 2115043 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:26])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)(=O)C.[Cl:39]C(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)([O-])O.[Na+]>[ClH:39].[CH2:27]([NH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:26])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][CH:7]=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 69100333HCID 69100333, compound

Product 1

HCID 69100529HCID 69100529, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 0.53 g (1.5 mmol) of N-(3-aminophenyl)-2-[4-(4-fluoro-benzyl)-piperidin-1-yl]-oxo-acetamide (Example 16), 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 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 treated with 2.5 N hydrochloric acid in ethylacetate to yield 0.39 g (54%) of the title compound. Melting Point: 206-213° 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. additionthe residue is treated with 2.5 N hydrochloric acid in ethylacetate

Sources & evidence

ORD record
ord-24b72c4f57ce4819a9bd214fe2e564a0
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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