Phenylacetaldehyde → HCID 69593417, compound

HRID 1839209Notes

Reaction equation

HRID 1839209 reaction equation
FC(F)(F)C(O)=O.C(O[C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][CH2:22][CH:23]([CH3:33])[C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:25])[CH2:16]1)=O)(C)(C)C.[C:34]1(CC=O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(O)(=O)C>[CH2:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][CH2:22][CH:23]([CH3:33])[C:24]([NH:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:25])[CH2:16]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

8

Reactant 5

HCID 998PhenylacetaldehydeHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 69593445HCID 69593445, compound

Product 1

HCID 69593417HCID 69593417, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (0.38 mL, 4.99 mmol) in CH2Cl2 (0.38 mL) was added dropwise to a 0° C. stirring solution of 101 (0.115 g, 0.318 mmol) in CH2Cl2 (0.40 mL). When the reaction was judged complete by TLC, the solvent and excess trifluoroacetic acid were removed in vacuo. The crude residue was dissolved in DMF (1.54 mL, 0.18M), then phenylacetaldehyde (0.10 mL, 0.832 mmol), acetic acid (0.078 mL), and Na(OAc)3BH (0.118 g, 0.555 mmol) were added sequentially. When the reaction was judged complete by TLC, saturated aqueous K2CO3 was added. The organic layer was removed, and 5% aqueous HCl was added. The organic layer was discarded, and the aqueous layer was basified with saturated aqueous NH4OH. The organic layer was removed, dried with Na2SO4, and concentrated in vacuo. Purification by silica gel chromatography (99:1::CH2Cl2:2N NH3 in EtOH) provided (1-benzylpiperidine-3-ylethyl)-N-phenylpropionamide (103). 1H NMR (CDCl3): 7.46-7.24 (8H, m), 7.15 (2H, broad d, J=7.8 Hz), 3.72 (2H, J=7.8 Hz), 3.52 (1H, J=13.2 Hz), 3.45 (1H, d, J=13.2 Hz), 2.79 (2H, broad d, J=8.2 Hz), 2.03 (2H, q, J=7.3 Hz), 1.91 (1H, td, J=11.0, 3.3 Hz), 1.84-1.30 (7H, m), 1.05 (3H, t, J=7.4 Hz), 0.98-0.84 (1H, m) ppm. 13C NMR (CDCl3): 173.65, 142.93, 138.4, 129.83, 129.35, 128.52, 128.31, 127.95, 127.07 63.68, 60.21, 54.22, 47.34, 34.14, 32.51, 30.84, 28.04, 25.34, 9.78 ppm. LRMS: 350.95.

Workup

  1. customthe solvent and excess trifluoroacetic acid were removed in vacuo
  2. dissolutionThe crude residue was dissolved in DMF (1.54 mL, 0.18M)
  3. additionwas added
  4. customThe organic layer was removed
  5. addition5% aqueous HCl was added
  6. customThe organic layer was removed
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel chromatography (99:1::CH2Cl2:2N NH3 in EtOH)

Sources & evidence

ORD record
ord-f0c512ab7fc84dcea3f05880bb3cace3
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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