HCID 46929757, compound → HCID 11637664, compound

HRID 1441930Notes

Reaction equation

HRID 1441930 reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19](=[O:27])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[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:27])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 46929757HCID 46929757, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11637664HCID 11637664, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of hexyl-carbamic acid 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-yl ester (0.732 g., 2 mmol) and 5% Pd—C (0.08 g.) in absolute ethanol (20 ml) was shaken in a par apparatus at room temperature (38° C.) under 50 psi pressure of hydrogen for 4 hours. Pd—C was then discarded through filtration. The reaction mixture was concentrated under vaccum and the separated solid was washed with chloroform (2×5 ml) to give 2a; yield: 0.60 g. (64.1%), m.p.: 100° C., C16H24N2O2; 1H NMR δ ppm (CDCl3): 0.88 (bs, 3H), 1.25-1.30 (m, 5H), 1.51-1.58 (m, 3H), 1.85-1.97 (m, 3H), 2.74 (t, 2H), 3.16-3.29 (m, 4H), 3.6 (bs, 1H), 4.87 (bs, 1H), 6.39-6.4 (m, 1H), 6.68-6.71 (m, 2H), IR vmax (KBr) (cm−1): 770, 816, 886, 956, 1006, 1101, 1152, 1221, 1243, 1311, 1354, 1505, 1626, 1702, 1848, 2372, 2856, 2929, 3392, 3760, 3809, 7874, MS: m/z: 277 (M+).

Workup

  1. filtrationPd—C was then discarded through filtration
  2. concentrationThe reaction mixture was concentrated under vaccum
  3. washthe separated solid was washed with chloroform (2×5 ml)

Sources & evidence

ORD record
ord-e2dc10dce34045fc9d767be2becf1740
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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