HCID 67492674, compound → HCID 67492899, compound

HRID 1922389Notes

Reaction equation

HRID 1922389 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])[CH2:4][CH2:3]1.[H][H]>[Pd].CCOC(C)=O.CO>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:6][CH2:7]1

Participants

6

Reactant 2

HCID 67492674HCID 67492674, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67492899HCID 67492899, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of (E)-methyl 3-(2-(1-methylpiperidin-4-ylamino)phenyl)acrylate (330 mg, 1.20 mmol) and palladium on carbon (10% wt, 128 mg, 0.12 mmol) in 20 mL EtOAc was stirred under a balloon of hydrogen overnight. The suspension was diluted with MeOH (50 mL) and filtered through a pad of celite. The celite pad was rinsed with 10 mL of MeOH. The filtrate was concentrated and the residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2. A light yellow oil was obtained (300 mg, 90.4%). 1H-NMR (CDCl3) δ 7.14-7.08 (m, 1H), 7.04-7.01 (m, 1H), 6.67-6.63 (m, 2H), 3.76-3.74 (m, 1H), 3.69 (s, 3H), 3.35 (brs, 1H), 2.82-2.77 (m, 4H), 2.65-2.60 (m, 2H), 2.31 (s, 3H), 2.19-2.06 (m, 4H), 1.61-1.49 (m, 2H). MS (ESI): 277.2 (M+1, 100%).

Workup

  1. filtrationfiltered through a pad of celite
  2. washThe celite pad was rinsed with 10 mL of MeOH
  3. concentrationThe filtrate was concentrated
  4. customA light yellow oil was obtained (300 mg, 90.4%)

Sources & evidence

ORD record
ord-3c6f3f9ea1534a8d84a207a149979c9f
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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