Hydrochloric Acid → N-(1-[2-Chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-3-(3-pyridyl)propionamide dihydrochloride

HRID 258295Notes

Reaction equation

HRID 258295 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([CH2:17][N:18]4[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:34])/[CH:26]=[CH:27]/[C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)[CH2:20][CH2:19]4)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1.[ClH:35]>C(O)C.[Pd].CCOCC.C(Cl)(Cl)Cl>[ClH:1].[ClH:35].[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]3[CH2:16][C:5]([CH2:17][N:18]4[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:34])[CH2:26][CH2:27][C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)[CH2:20][CH2:19]4)([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86747398N-(1-[2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-trans-3-(3-pyridyl)propenamide

Product 1

HCID 19381050N-(1-[2-Chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-3-(3-pyridyl)propionamide dihydrochlorideYield 52%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 21911965Chloroform etherSolvent

Procedure

To a stirred solution of N-(1-[2-chloro-9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-trans-3-(3-pyridyl)propenamide (170 mg, 0.36 mmol) in ethanol (5 mL) was added 10% palladium on carbon (17 mg). This mixture was hydrogenated at 1 atmospheric pressure for 18 h. The reaction was filtered through diatomaceous earth. The filtrate was concentrated and the resulting residue was chromatographed over silica gel (eluant: 95:5 methylene chloride:methanol) to give a white foam. This material was dissolved in a cold (ice bath) solution of ether:chloroform (3:1, v/v, 15 mL) and treated with gaseous hydrochloric acid to afford the title compound as a white solid (100 mg, 52%), mp 220.0°-3.0° C.; MS(CI): 472 (M+H); NMR (300 MHz,DMSO-d6): 1.65-2.06(m, 4H), 2.46(t, 1.70H, J=7.5 Hz), 2.59(t, 0.3H, J=7.5 Hz), 2.73(m, 2H), 2.87-3.03(m, 2H), 3.17-3.66(m, 4H), 3.78(br m, 0.85H), 3.96(m, 0.15H), 4.18-4.40(m, 2H), 4.48(s, 1H), 6.95-7.10(m, 3H), 7.27-7.42(m, 3H), 7.48(s, 1H), 7.59-7.71(m, 1H), 8.02(d, 1H, J=7.5 Hz), 8.11 (d, 1H, J=7.2 Hz), 8.35(br s, ~0.15H), 8.54-8.65(m, 2H), 8.68(br s, ~0.85H), 9.70(br s, 0.15H), 9.96-10.08(br s, 0.85H).

Workup

  1. filtrationThe reaction was filtered through diatomaceous earth
  2. concentrationThe filtrate was concentrated
  3. customthe resulting residue was chromatographed over silica gel (eluant: 95:5 methylene chloride:methanol)
  4. customto give a white foam

Sources & evidence

ORD record
ord-eadaa891d291467ea4e39bda0dc5c79c
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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