8-Benzyl-3-(4-chlorophenyl)-3,8-diazabicyclo[3.2.1]octane → 3-(4-Chlorophenyl)-3,8-diazabicyclo[3.2.1]octane hydrochloride

HRID 1860378Notes

Reaction equation

HRID 1860378 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:12]2)C1C=CC=CC=1>[Pd].Cl.CO>[ClH:22].[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([N:11]2[CH2:10][CH:9]3[NH:8][CH:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 98579668-Benzyl-3-(4-chlorophenyl)-3,8-diazabicyclo[3.2.1]octane

Product 1

HCID 185451893-(4-Chlorophenyl)-3,8-diazabicyclo[3.2.1]octane hydrochlorideYield 198.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21893726Hydrochloride methanolSolvent

Procedure

8-Benzyl-3-(4-chlorophenyl)-3,8-diazabicyclo[3.2.1]octane (8.5 g, 27.17 mmol) and 10% palladium on carbon (8.5 g) were combined in 1N hydrochloric acid/methanol (600 ml). The mixture was hydrogenated at atmospheric pressure for 4 hours under hydrogen gas. The reaction was filtered through Celite and the filtrate was concentrated to yield 3-(4-chlorophenyl)-3,8-diazabicyclo[3.2.1]octane hydrochloride (7.0 g, 100%) as an off-white solid. A portion recrystallized from water yielded white crystalline flakes which had the following properties: M.p. 270-275° C.; 1H NMR (CDCl3) δ: 9.70 (brd s, 2H), 7.22 (d, J=9.1 Hz, 2H), 6.87 (d, J=8.7 Hz, 2H), 4.06 (brd s, 2H), 3.55 (d, J=11.6 Hz, 2H), 3.12 (d, J=12 Hz, 2H), 2.01-1.79 (m, 4H); IR (KBr): 3969, 3913, 3862, 3739, 3670, 3194, 3094, 2990, 2972, 2947, 2867, 2778, 2748, 2696, 2657, 2609, 2574, 2537, 2500, 2431, 2396, 2384, 2252, 2133, 2092, 2078, 2033, 1991, 1951, 1922, 1903, 1873, 1799, 1750, 1688, 1600, 1570, 1500, 1460, 1421, 1383, 1367, 1344, 1323, 1269, 1252, 1220, 1207, 1165, 1155, 1120, 1099, 1079, 1059, 1012, 1001, 978, 937, 922, 904, 872, 828, 817, 808, 783, 749, 700, 651, 632, 534, 520, 468, 415, 403, (cm−1); Elemental Analysis, Calculated for C12H16CIN2: C, 55.61; H, 6.23; N, 10.81; Found: C, 55.35, H, 6.21, N, 10.79.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0b0c1768562d40e0ad25d4b4ac740e6b
Source dataset
uspto-grants-2003_03
Patent number
US06531468B2

Reaction notes

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