HCID 11552653, compound → HCID 11507563, compound

HRID 1441931Notes

Reaction equation

HRID 1441931 reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19](=[O:28])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19](=[O:28])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 11552653HCID 11552653, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11507563HCID 11507563, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A nitrogen flushed mixture of heptyl-carbamic acid 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester (0.378 g., 1 mmol) and 10% Pd—C (0.02 g.) in absolute ethanol (20 ml) was shaken in a par apparatus at room temperature (38° C.) under 55 psi pressure of hydrogen for 4 hours. Pd—C was then discarded through filtration. The reaction mixture was concentrated under reduced pressure and the residue was chromatographed with methanol: dichloromethane (1:99) to give 2b; yield: 0.25 g. (84.6%), m.p.: 67° C., C17H26N2O2; 1H NMR δ ppm (CDCl3): 0.88 (bs, 3H), 1.20-1.30 (m, 7H, 1.56 (bs, 3H), 1.88-1.93 (m, 2H), 2.74 (t, 2H), 3.23-3.28 (m, 4H), 3.66-3.76 (m, 1H), 4.89 (bs, 1H), 6.40-6.44 (m, 1H), 6.68-6.71 (m, 2H); IR vmax (KBr) (cm−1): 561, 665, 768, 815, 887, 976, 1149, 1223, 1308, 1353, 1506, 1621, 1699, 2362, 2857, 2930, 3763.

Workup

  1. customA nitrogen flushed
  2. filtrationPd—C was then discarded through filtration
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was chromatographed with methanol: dichloromethane (1:99)

Sources & evidence

ORD record
ord-570090f8be434a26a17aed31e5e06e09
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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