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Phenylacetaldehyde → N-(1-Phenethyl-piperidin-3-ylmethyl)-N-phenyl-propionamide

HRID 988761
Notes
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Reaction equation

HRID 988761 reaction equation
FC(F)(F)C(O)=O.[C:8]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][N:22]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:23](=[O:26])[CH2:24][CH3:25])[CH2:16]1)(OC(C)(C)C)=O.[C:33]1([CH2:39]C=O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:8]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([CH2:21][N:22]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:23](=[O:26])[CH2:24][CH3:25])[CH2:16]1)[CH2:39][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 998PhenylacetaldehydeHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 12991578N-(1-Boc-piperidin-3-ylmethyl)-N-phenyl-propionamide

Product 1

HCID 9950309N-(1-Phenethyl-piperidin-3-ylmethyl)-N-phenyl-propionamide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Trifluoroacetic acid (5 mL) was added dropwise to a solution of N-(1-Boc-piperidin-3-ylmethyl)-N-phenyl-propionamide 5 (1.21 g, 3.49 mmol) in 5 mL of dry CH2Cl2 at 0° C. (ice-water). The reaction mixture was stirred at room temperature for 30 minutes. TLC showed the reaction was complete. After removal of the solvents, the residue was dried under vacuum for 3 hrs. The crude compound was dissolved in DMF (5.0 mL) and phenylacetaldehyde (5.3 mL, 2 M/in DMF, 5.3 mmol) was added. The mixture was stirred at room temperature for 30 min. NaB(OAc)3H (95%, 1.18 g, 5.3 mmol.) was introduced in one portion, and the mixture was stirred at room temperature overnight. The mixture was quenched with 10 mL of aqueous potassium carbonate (sat.), then extracted with ethyl acetate (3×60 mL). The extracts were combined and washed with aqueous NaHCO3 (sat., 2×10 mL), brine (30 mL), and dried over anhydrous sodium sulfate. After the solvent was removed, the remaining oily residue was purified by a flash column chromatography to give 6. IR (film, cm−1) 3060, 3026, 2934, 2854, 2800, 2765, 1662, 1495, 1452, 1401, 1262, 1203, 1150, 1106, 966, 1033, 775, 749; LRMS 351.

Workup

  1. customAfter removal of the solvents
  2. customthe residue was dried under vacuum for 3 hrs
  3. dissolutionThe crude compound was dissolved in DMF (5.0 mL)
  4. stirringThe mixture was stirred at room temperature for 30 min
  5. stirringthe mixture was stirred at room temperature overnight
  6. customThe mixture was quenched with 10 mL of aqueous potassium carbonate (sat.)
  7. extractionextracted with ethyl acetate (3×60 mL)
  8. washwashed with aqueous NaHCO3 (sat., 2×10 mL), brine (30 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customAfter the solvent was removed
  11. customthe remaining oily residue was purified by a flash column chromatography
  12. customto give 6

Sources & evidence

ORD record
ord-245dbf6ae13f4c718e4d4a4f72908195
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06635661B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes