Propionyl chloride → N-(1-Benzyl-piperidin-3-yl)-N-phenyl-propionamide

HRID 479831Notes

Reaction equation

HRID 479831 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:30](Cl)(=[O:33])[CH2:31][CH3:32]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:30](=[O:33])[CH2:31][CH3:32])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 113914823-Piperidinamine, N-phenyl-1-(phenylmethyl)-

Product 1

HCID 12741868N-(1-Benzyl-piperidin-3-yl)-N-phenyl-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the crude (1-benzyl-piperidin-3-yl)-phenyl-amine (164) (1.11 g) in CH2Cl2 (5 ml) at 0° C. was added i-Pr2NEt (1.45 ml) and propionyl chloride (0.54 ml). The mixture was stirred for 2 hr. The mixture was diluted with CH2Cl2 (20 ml), washed with sat. NaHCO3 (2×10 ml), brine (10 ml) and water (10 ml) and dried with Na2SO4. After filtration, the filtrate was concentrated under vacuum. The residue was purified by silica gel chromatography (0.5% to 2% MeOH in CH2Cl2) to give 165 as a colorless oil. LRMS (calculated for C21H26N2O) 322, found 322; IR (film) 3059, 2937, 2863, 2797, 1657, 1594, 1499, 1390, 1264, 1101, 1074, 739, 703 cm−1.

Workup

  1. washwashed with sat. NaHCO3 (2×10 ml), brine (10 ml) and water (10 ml)
  2. dry with materialdried with Na2SO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe residue was purified by silica gel chromatography (0.5% to 2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-426df57a5bc9417189ef448858c5bae1
Source dataset
uspto-grants-2003_11
Patent number
US06645980B1

Reaction notes

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