Hydrochloric Acid → HCID 68576445, compound

HRID 273060Notes

Reaction equation

HRID 273060 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4([C:26]#[N:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[CH2:9]2)C=CC=CC=1.Cl>[OH-].[Pd+2].[OH-].C(O)C>[NH:8]1[CH2:11][CH:10]([CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3([C:26]#[N:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:18][CH:19]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68576812HCID 68576812, compound

Product 1

HCID 68576445HCID 68576445, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

4-(4-{[1-(diphenylmethyl)azetidin-3-yl]methoxy}phenyl)tetrahydro-2H-pyran-4-carbonitrile (0.605 g, 1.38 mmol), palladium hydroxide (0.08 g), concentrated hydrochloric acid (0.115 mL, 1.38 mmol), and ethanol (8 mL) were combined and hydrogenated for 18 hours at 40° C. at 40 psi. The mixture was filtered through Arbocel® and rinsed with ethanol. The filtrate was concentrated in vacuo. The residue was dissolved in DCM (50 mL) and washed with 10% aqueous sodium carbonate (20 mL). The organics were dried over sodium sulphate, filtered and concentrated in vacuo to provide a green oil. This was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 to 90:10:1) to provide the title compound (0.145 g, 39%) as a yellow oil. LRMS APCI+ m/z 273 [MH]+.

Workup

  1. filtrationThe mixture was filtered through Arbocel®
  2. washrinsed with ethanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in DCM (50 mL)
  5. washwashed with 10% aqueous sodium carbonate (20 mL)
  6. dry with materialThe organics were dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto provide a green oil
  10. customThis was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 to 90:10:1)

Sources & evidence

ORD record
ord-0dd3e43a77114e269c4bc3a88946589e
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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