Hydrochloric Acid → HCID 18679302, compound

HRID 1633451Notes

Reaction equation

HRID 1633451 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][CH2:24][CH:23]=[CH:22][C:17]4=3)[N:12]([CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:37]>C(O)C.[Pd]>[ClH:37].[O:30]([CH2:29][CH2:28][CH2:27][CH2:26][N:12]1[C:13]2[C:18](=[C:17]3[CH2:22][CH2:23][CH2:24][O:25][C:16]3=[CH:15][CH:14]=2)[C:19]2[CH2:20][CH2:21][NH:8][CH2:9][CH2:10][C:11]1=2)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10116596HCID 10116596, compound

Product 1

HCID 18679302HCID 18679302, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution containing 10-benzyl-7-(4-phenoxybutyl)-7,8,9,10,11,12-hexahydro-3H-azepino[4,5-b]pyrano[3,2-e]indole (0.085 g., 0.18 mmol, Example 5) in ethanol (10.0 mL) was hydrogenated in the presence of palladium-on-carbon (0.04 g.) and 2 N hydrochloric acid (0.09 mL, 0.18 mmol) at 50 psi for 16 hours. After filtration through a pad of celite, the filtrate was concentrated in vacuo. The residue was recrystalized from EtOAc/MeOH to yield the title compound (0.075 g, 99%) as a light yellow solid. 1H NMR (300 MHz, MeOH-d4) δ 7.24-7.19, 7.03, 6.90-6.80, 6.57, 4.18-4.06, 3.85, 3.47-3.32, 3.28-3.17, 3.11, 2.04-1.95, 1.89-1.65, 1.40-1.25, 0.95-0.81; MS (ESI+) m/z 391 (M++H).

Workup

  1. filtrationAfter filtration through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was recrystalized from EtOAc/MeOH

Sources & evidence

ORD record
ord-cc49d8deb5064fb3a190459cbf37c926
Source dataset
uspto-grants-2003_01
Patent number
US06503899B2

Reaction notes

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