Hydrochloric Acid → HCID 18679301, compound

HRID 1633449Notes

Reaction equation

HRID 1633449 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)[NH:12][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:26]>C(O)C.[Pd]>[ClH:26].[CH2:22]1[C:17]2=[C:18]3[C:13](=[CH:14][CH:15]=[C:16]2[O:25][CH2:24][CH2:23]1)[NH:12][C:11]1[CH2:10][CH2:9][NH:8][CH2:21][CH2:20][C:19]3=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9862338HCID 9862338, compound

Product 1

HCID 18679301HCID 18679301, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10-benzyl-7,8,9, 10,11,12-hexahydro-3H-azepino[4,5-b]pyrano[3,2-e]indole (0.38 g., 1.17 mmol, Example 3) in ethanol (20.0 mL) was hydrogenated in the presence of palladium-on-carbon (0.20 g.) and 2N hydrochloric acid (0.58 mL, 1.17 mmol) at 55 psi for 24 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 (0.31 g, 94%) as a light yellow solid. M.p.>283° C. (dec.); IR (KBr) 3235, 3229, 2983, 2957, 2946, 2926, 2877, 2855, 2817, 2752, 2738, 2717, 2681, 2639, 2600, 2540, 1585, 1497, 1454, 1435, 1430, 1225, 1186, 1089, 805 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 10.82, 9.55, 6.95, 6.48, 4.04-4.02, 3.30-3.23, 3.13-3.10, 3.07-3.04, 1.99-1.93; 13C NMR (DMSO-d6) δ 147.7, 135.1, 129.4, 125.9, 111.6, 111.5, 110.2, 109.6, 64.8, 46.3, 44.4, 24.3, 22.7, 22.5, 22.2; MS (ESI+) m/z 243 (M++H); HRMS (FAB) cacld for C15H18N2O+H: 243.1497, found: 243.1500; Anal. Calcd. for C15H18N2O.HCl: C, 64.63; H, 6.87; N, 10.05. Found: C, 64.23; H, 6.95; N, 9.87.

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-d9c984c5f9e948c294605bda1eb774fe
Source dataset
uspto-grants-2003_01
Patent number
US06503899B2

Reaction notes

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