Hydrochloric Acid → HCID 69966628, compound

HRID 1633454Notes

Reaction equation

HRID 1633454 reaction equation
C([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]4[O:25][C:24]([CH3:27])([CH3:26])[CH:23]=[CH:22][C:17]4=3)[NH:12][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:28]>C(O)C.[Pd]>[ClH:28].[CH3:26][C:24]1([CH3:27])[O:25][C:16]2[C:17](=[C:18]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11]2[CH2:10][CH2:9][NH:8][CH2:21][CH2:20][C:19]3=2)[CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9924971HCID 9924971, compound

Product 1

HCID 69966628HCID 69966628, compoundYield 30.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of 10-benzyl-3,3-dimethyl-7,8,9,10,11,12-hexahydro-3H-azepino[4,5-b]pyrano[3,2-e]indole (0.065 g, 0.18 mmol, Example 11) in ethanol (20.0 mL) was hydrogenated in the presence of palladium on carbon (0.035 g) and 2 N hydrochloric acid (0.09 mL, 0.1 8 mmol) at 55 psi for 3 days. Palladium on carbon (0.035 g) was added and continued hydrogenation for another 4 days. After filtration through a pad of celite, the filtrate was concentrated in vacuo to dryness. The residue was recrystallized from EtOAc/MeOH to give 0.017 g (30%) of colorless solid as the desired product: mp>258° C. (dec.); 1H NMR (300 MHz, MeOH-d4) δ 7.00, 6.52, 3.47, 3.22-3.13, 1.89-1.85, 1.33; MS (ESI+) m/z 271 (M++H).

Workup

  1. customfor another 4 days
  2. filtrationAfter filtration through a pad of celite
  3. concentrationthe filtrate was concentrated in vacuo to dryness
  4. customThe residue was recrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-351d412ff9fb4c509579365b949a512a
Source dataset
uspto-grants-2003_01
Patent number
US06503899B2

Reaction notes

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