Hydrochloric Acid → HCID 18679314, compound

HRID 1633448Notes

Reaction equation

HRID 1633448 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]([CH3:26])[C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:27]>C(O)C.[Pd]>[ClH:27].[CH3:26][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

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9902718HCID 9902718, compound

Product 1

HCID 18679314HCID 18679314, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution containing 10-benzyl-7-methyl-7,8,9,10,11,12-hexahydro-3H-azepino[4,5-b]pyrano[3,2-e]indole (0.18 g., 0.51 mmol, Example 1) in ethanol (20.0 mL) was hydrogenated in the presence of palladium-on-carbon (0.07 g.) and 2 N hydrochloric acid (0.51 mL, 0.51 mmol) at 50 psi for 48 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 (0.13 g, 84%) as a light yellow solid. M.p.>217° C. (dec.); IR (KBr) 2946, 2877, 2844, 2809, 1609, 1585, 1551, 1467, 1447, 1280, 1267, 1255, 1238, 1109, 787 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 7.07, 6.52, 4.04-4.01, 3.57, 3.31-3.28, 3.19-3.12, 3.07-3.03, 1.96-1.92; 13C NMR (DMSO-d6) δ 148.5, 136.8, 131.2, 125.2, 112.3, 112.1, 110.9, 108.8, 65.4, 46.3, 44.2, 29.7, 23.1, 22.6, 22.4; MS (ESI+) m/z 257 (M++H); HRMS cacld for C16H20N2O+H: 257.1654, found: 257.1646; Anal. Calcd. for C16H20N2O.HCl.H2O: C, 61.83; H, 7.46; N, 9.01. Found: C, 62.07; H, 7.41; N, 9.01.

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-7df13cec9b0649d4bb2542ddfffe33d6
Source dataset
uspto-grants-2003_01
Patent number
US06503899B2

Reaction notes

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