Hydrochloric Acid → 2-(Trimethylsilyl)ethyl 4-(3-(aminomethyl)phenyl)-piperidine-1-carboxylate hydrochloride

HRID 489621Notes

Reaction equation

HRID 489621 reaction equation
[CH3:1][Si:2]([CH3:23])([CH3:22])[CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7].[ClH:24]>C(O)C.[Pd]>[ClH:24].[CH3:1][Si:2]([CH3:23])([CH3:22])[CH2:3][CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH2:21])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 601143952-(Trimethylsilyl)ethyl 4-(3-cyanophenyl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 690309902-(Trimethylsilyl)ethyl 4-(3-(aminomethyl)phenyl)-piperidine-1-carboxylate hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(3-Cyanophenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (10.40 g, 32 mmol) was dissolved in ethanol (250 ml), concentrated hydrochloric acid (3 ml, 35 mmol) and 10% palladium on carbon (50% wet, 5.0 g) was added. The mixture was hydrogenated at 50 psi for 4 hours then filtered through celite and concentrated. The oily solid obtained was triturated with ether/pentane and 4-(3-aminomethyl-phenyl)-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester hydrochloride was obtained as a white solid (7.10 g). 1H NMR [(CD3)2SO, 300 MHz]: δ 8.38 (br s, 2H), 7.20-7.40 (m, 4H), 4.10 (t, 4H), 3.98 (s, 2H), 2.63-3.00 (m, 3H), 1.75 (m, 2H), 1.50 (m, 2H), 0.94 (t, 2H), 0.02 (s, 9H). LC-MS (ES) 335 (M++H), 93% TIC.

Workup

  1. filtrationthen filtered through celite
  2. concentrationconcentrated
  3. customThe oily solid obtained
  4. customwas triturated with ether/pentane

Sources & evidence

ORD record
ord-b03ed78bdd2e4d24b6927bd6f293c4c3
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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