Hydrochloric Acid → HCID 22265958, compound

HRID 489600Notes

Reaction equation

HRID 489600 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2([C:22]#[N:23])[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.[H][H]>C(O)C.[Pd]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([C:9]2([C:22]#[N:23])[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH2:14]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 22265879tert-Butyl 4-cyano-4-(3-cyanophenyl)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22265958HCID 22265958, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 0.31 g (1 mmole) of 4-(3-cyanophenyl)-1-tert-butoxycarbonyl-piperidine-4-carbonitrile in 30 ml of absolute ethanol was added 0.08 ml (1 mmole) of conc. hydrochloric acid followed by 30 mg of 5% Pd/C. The mixture was agitated in a Parr shaker for 3 hours at 30 lbs. of pressure of hydrogen. The mixture was filtered through celite and the filtrate was evaporated. The residue was treated with ether and was stirred for 30 minutes and was filtered. The filter cake was treated with aqueous sodium carbonate and was extracted with dichloromethane to give 0.2 g of product: 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.38-1.60(m, 9H), 1.88-2.18(m, 4H), 3.05-3.30(m, 4H), 3.79-4.0(m, 2H), 7.22-7.85(m, 4H); MS (ESI) m/e 316 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate was evaporated
  3. additionThe residue was treated with ether
  4. stirringwas stirred for 30 minutes
  5. filtrationwas filtered
  6. additionThe filter cake was treated with aqueous sodium carbonate
  7. extractionwas extracted with dichloromethane

Sources & evidence

ORD record
ord-c12b08f91ff24e4d92fd8631f364fadf
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

Loading…